Substituted fused heterocyclic herbicides

ABSTRACT

This invention relates to substituted fused heterocyclic compounds of Formula I which have utility as herbicides: ##STR1##

CROSS-REFERENCE TO RELATED APPLICATION

This application is a divisional of application Ser. No. 08/050,475, filed May 21, 1993, now U.S. Pat. No. 5,389,600, granted Feb. 14, 1995, which is a 371 of PCT/US91/08266, filed Nov. 14, 1991, which is a continuation-in-part of application Ser. No. 07/617,707 filed Nov. 26, 1990, now U.S. Pat. No. 5,110,347, granted May 5, 1992.

BACKGROUND OF THE INVENTION

This invention relates to certain substituted fused heterocyclic compounds which are useful as herbicides and their agriculturally suitable compositions as well as methods for their use as general or selective preemergent or postemergent herbicides or as plant growth regulants.

New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.

EP-A-353,902 discloses herbicidal compounds of the formula ##STR2## wherein, inter alia G and G¹ are N and C; and

X, Y and Z are independently CR₇ or N.

Ind. J. Chem. 1980, 19B, 1011-1013 discloses without teaching herbicidal utility compounds of the formula ##STR3##

SUMMARY OF THE INVENTION

This invention comprises compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as preemergence and/or postemergence herbicides or plant growth regulants. ##STR4## wherein X is N or CH;

Y is N or CR⁸ ;

Z is N, CR⁴ or CR⁵ ;

Q i s N, CR⁴ or CR⁵ ;

R is C₁ -C₄ alkyl, C₂ -C₄ alkoxyalkyl, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl, C₁ -C₄ alkoxy,, C₁ -C₄ alkylthio, C₁ -C₃ alkylamino or N(C₁ -C₃ alkyl) (C₁ -C₃ alkyl);

R¹ is H, F, Cl or CH₃ ;

R² is H, halogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy;

R³ is H, halogen, C₁ -C₄ alkyl, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl, C₁ -C₄ haloalkyl, C₃ -C₄ halocycloalkyl, C₂ -C₄ haloalkenyl, C₂ -C₄ haloalkynyl, OR⁶, S(O)_(n) R₇ or CN;

R⁴ is H, CN, C₁ -C₃ alkyl, C₁ -C₃ alkoxy or halogen;

R⁵ is C₁ -C₄ haloalkyl, C₃ -C₅ halocycloalkyl, C₂ -C₄ haloalkenyl, C₂ -C₄ haloalkynyl, OR⁶, S(O)_(n) R⁷ or halogen;

R⁶ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, C₁ -C₄ haloalkyl, C₂ -C₄ haloalkenyl or C₂ -C₄ haloalkynyl;

R⁷ is C₁ -C₂ alkyl or C₁ -C₂ haloalkyl;

R⁸ is H, CN, C₁ -C₃ alkyl, C₁ -C₃ alkoxy or halogen; and

n is 0, 1 or 2.

and their mono N-oxides and their agriculturally suitable salts, provided that:

(a) when Z is N or CR⁴, then Q is CR⁵ ; and

(b) when Q is N or C R⁴, then Z is CR⁵.

In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers. "Alkoxy", "alkenyl" and "alkynyl" analogously also includes straight chain or branched isomers. "Halogen", either alone or in compound words such as "haloalkyl", means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples include CF₃, CH₂ CF₃, CH₂ CH₂ F, CF₂ CF₃ and CH₂ CHFCl.

Preferred for reasons including ease of synthesis and/or greater herbicidal efficacy are:

1. Compounds of Formula I wherein

R¹ is H or F; and

R² is H or F.

2. Compounds of Preferred 1 wherein

R³ is F, Cl, Br, C₁ -C₄ haloalkyl, OR⁶, S(O)_(n) R⁷ or CN;

n is O;

Y is N, CH or C--CN; and their mono N-oxides.

3. Compounds of Preferred 2 wherein

R is C₁ -C₃ alkyl, C₂ -C₃ alkoxyalkyl, C₂ -C₃ alkenyl, C₂ -C₃ alkynyl, C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₁ -C₂ alkylamino and N(C₁ -C₂ alkyl) (C₁ -C₂ alkyl);

R⁶ is C₁ -C₃ alkyl, allyl, propargyl, C₁ -C₃ haloalkyl, C₂ -C₃ haloalkenyl.

4. Compounds of Preferred 3 wherein

Z is N, CH or C--CN.

Specifically Preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are:

2-(difluoromethoxy)-6-methyl-8-[3-(trifluoromethyl)phenyl]quinoxaline;

7-methyl-3-(2,2,2-trifluoroethoxy)-5-[3-(trifluoromethyl)phenyl]-1,2,4-benzotriazine 1-oxide;

7-methyl-3-(2,2,2-trifluoroethoxy)-5-[3-(trifluoromethyl)phenyl]-1,2,4-benzotriazine; and

6-methyl-2-(trifluoromethyl)-8-[3-(trifluoromethyl)phenyl]quinoxaline.

DETAILED DESCRIPTION OF THE INVENTION

Compounds of General Formula I can be readily prepared by one skilled in the art by using the reactions and techniques described in Schemes 1-10 and Equations 1-5 of this section as well as by following the specific procedures given in Examples 1-7.

Scheme 1 illustrates the preparation of compounds of General Formula I (where R, R¹, R², R³ X, Y, Z, and Q are defined as above) whereby heterocycles of Formula II where G is bromine or iodine can be coupled with substituted aryl compounds of Formula III where J is a trialkyltin (e.g. Me₃ Sn), trialkylsilyl (e.g. Me₃ Si), or a boronic acid (e.g. B(OH)₂) moiety. The coupling is carried out using methods known in the art: Tsuji, J., Organic Synthesis with Palladium Compounds, Springer-Verlag, Berlin, 1980; Negishi, E., Acc. Chem. Res. 1982, 15, 340; Stille, J. K., Angew. Chem. 1986, 98, 504; Yamamoto, A., Yamagi, A., Chem. Pharm. Bull. 1982, 30, 1731 and 2003; Dondoni, A., Fogagnolo, M., Medici, A., Negrini, E., Synthesis 1987, 185; Dondoni, A., Fantin, G., Fogagnolo, M., Medici A., Pedrini, P., Synthesis 1987, 693; Hoshino, Y., Miyaura, N., Suzuki, A., Bull. Chem. Soc. Jpn. 1988, 61, 3008; Sato, M., Miyaura, N., Suzuki, A., Chem. Lett. 989, 1405 ; Miyaura, N., Yanagi, T., Suzuki, A. Synthetic Commun. 1981, 11, 513; Siddiqui, M. A., Snieckus, V., Tetrahedron Lett. 1988, 29, 5463; Sharp, M. J., Cheng, W., Snieckus, V., Tetrahedron Lett. 987, 28, 5093; Hatanaka, Y., Fukushima, S., Hiyama, , T., Chem. Lett. 989, 1711; Bailey, T. R., Tetrahedron Lett. 1986, 27, 407. The coupling of II and III is carried outby heating in the presence of a transition metal catalyst such as tetrakis (triphenylphosphine) palladium(0) or bis(triphenylphoshine)palladium(II) dichloride in a polar or nonpolar aprotic solvent such as acetonitrile or toluene. As shown in Scheme 1, compounds of General Formula I can also be prepared by coupling heterocylic compounds of Formula IV where J is a trialkyltin (e.g. Me₃ Sn), trialkylsilyl (e.g. Me₃ Si), or boronic acid (e.g. B(OH)₂) moiety with aryl halides of Formula V where G is bromine or iodine using the same conditions as described above. ##STR5##

Heterocycles of Formula II can be prepared by the methods summarized in Schemes 2-10 and Equations 1-5. By methods also reported in the above cited art, treatment of heterocycles of Formula II where G is hydrogen, bromine, or iodine with base such as n-butyl lithium followed by quenchingwith a trialkyltin halide, trialkylsilyl halide, or trialkyl borate gives heterocylic intermediates of Formula IV. Substituted aryl compounds of Formula III and V are either known or readily prepared by methods given inthe above references.

As illustrated in Scheme 2, quinolines of Formula IIa and IIb can be prepared by reaction of anilines of Formula VI with substituted acroleins,vinyl ketones, and diketones of Formulas VIIa and VIId where R⁴ and R⁸ are hydrogen or alkyl, R⁵ is haloalkyl, haloalkenyl, haloalkynyl, or halocycloalkyl and R, R¹, and G are as previously defined. By the methods of Skraup (Chem. Bet. 1880, 13, 2086; 1882, 15, 987) and Combs (Compt. rend. 1887, 106, 142; Bull. Soc. Chim. France, 1888, 49, 90), anilines VI can be heated neat with compounds VIIa and VIIdfollowed by treatment with a strong inorganic acid such as sulfuric acid togive IIa and IIb. ##STR6##

Scheme 3 illustrates the synthesis of quinolines IIa and IIc where R⁴ and R⁸ are hydrogen or alkyl, R⁵ is OR⁶, SR⁷ or chlorine, and R, R¹ and G are as defined above. Reaction of anilines of Formula VI with substituted cinnamoyl chlorides of Formula VIIIa with abase such as pyridine with or without a solvent such as methylene chloride or tetrahydrofuran gives cinnamides of Formula VIIIb which can then be treated with an excess of a Lewis acid such as aluminum trichloride using the conditions of Johnston et al (J. Chem. Soc. Perkin I 1972, 1648) to give hydroxyquinolines of Formula VIIIc. Heating VIIIc in thionyl chlorideor phosphorous oxychloride gives chloroquinolines IIc. Displacement of the chloro group with R⁶ O⁻ M⁺ or R⁷ S⁻ M⁺ (where M is an alkali or alkaline metal such as sodium, potassium, or lithium and R⁶ and R⁷ are as previously defined) affords quinolines IIa where R⁵ is OR⁶ or SR⁷. Alkylation of VIIIc with R⁶ L (where L is a leaving group such as halogen, e.g. bromine or chlorine) in the presence of a base such as triethylamine or sodium hydroxide can also give IIa where R⁵ is OR⁶ . Reaction of VIIIc with phosphorous pentasulfide in a solvent such as pyridine affords mercaptopyridines of Formula VIIId which on alkylation with R⁷ L (L is as described above) gives IIa where R⁵ is SR7. Oxidation of IIa where R⁵ is SR⁷ with an oxidizing agent such as metachloroperoxy-benzoic acid gives quinolines of Formula IIa where R⁵ is S(O)R⁷ or S(O)₂ R⁷. ##STR7##

Quinolines of Formula IIb where R⁴ is alkoxy or halogen and R⁵ ishaloalkyl, haloalkenyl, haloalkynyl, or cyclohaloalkyl, R⁸ is hydrogenor alkyl and R, R¹, and G are as defined above can be made from the starting materials VI and cinnamoyl chlorides of Formula VIIIe (Equation 1) using the same chemistry as shown in Scheme 3. ##STR8##

Quinoxalines and pyridopyrazines of Formula IId and IIe where X is CH or N,R⁴ is hydrogen or alkyl, R⁵ is haloalkyl, haloalkenyl, or haloalkynyl, and R, R¹, and G are as previously defined can be made by the procedure shown in Scheme 4. ##STR9##Reduction (e.g. catalylic hydrogenation with palladium on carbon in a solvent such as tetrahydrofuran or ethanol) of nitroanilines and nitropyridinyl amines of Formula VIa gives phenylenediamines and diaminopyridines of Formula VIb. By the methods related to that of Jones et al (Org. Syntheses 1950, 30, 86), Gabriel et al (Chem. Ber. 1907, 40, 4850), and Bottcher (Chem. Ber. 1913, 46, 3084), condensation of VIb with a-diketones and a-ketoaldehydes of Formula IX in a nonpolar or polar protic or aprotic solvent such as ethanol, water, or tetrahydrofuran affords heterocycles IId and IIe.

Schemes 5 and 6 illustrate the syntheses of quinoxalines and pyridopyrazines of Formula IId and IIe where R⁵ is halogen, OR⁶ or SR⁷ and X, R, R¹, R⁴, and G are defined as above. Condensation of compounds of Formula VIb with a-aldo and a-ketoesters of Formula IXa (Scheme 5) by a method similar to that of Hinsberg (Chem. Ber.1884, 18, 1228) in a polar protic or aprotic solvent such as ethanol, wateror tetrahydrofuran gives hydroxyheterocycles of Formula IXb and IXc. Ethyl ester analogs of IXa can also be readily used in this condensation. Treatment of these hydroxyheterocycles with thienyl chloride or phosphorous oxychloride gives the chloroheterocycles IIf and IIg. Displacement of the chloro substituent with R⁶ O⁻ M⁺ or R⁷ S⁻ M⁺ (where M is an alkali or alkaline metal such as sodium, potassium, or lithium) yields compounds IId and IIe (where R⁵is OR⁶ or SR⁷). ##STR10##

Scheme 6 demonstrates that hydroxyheterocycles IXb and IXc can also be converted to compounds IId and IIe using similar chemistry as that shown in Scheme 3. Preparation of compounds IId and IIe where R⁵ is R⁷S involve making intermediate mercaptoheterocycles IXd and IXe. ##STR11##

Equation 2 illustrates that compounds IId and IIe where R⁴ is alkoxy and R⁵ is haloalkyl, halocycloalkyl, haloalkenyl, or haloalkynyl and R, R¹, X, and G are as defined above can be made from the starting materials VIb and the a-ketoesters IXf using the same chemistry as that inSchemes 5 and 6. ##STR12##

By a method similar to that reported by Reich et al (J. Med. Chem. 1989, 32, 2474), Scheme 7 summarizes the preparation of benzotriazines and pyridotriazines of Formula IIh where R⁵ is haloalkyl, halocycloalkyl,haloalkenyl, or haloalkynyl and R, R¹, G, and X are as defined above. Reaction of nitrophenyl hyrazines and nitropyridinyl hydrazines of FormulaX with an acid chloride of Formula Xa in a polar protic or aprotic solvent such as ethanol or acetonitrile gives hydrazide hydrochlorides of Formula Xb which can undergo catalytic hydrogenation using palladium on carbon or other suitable transition metal catalyst in a polar protic solvent such asethanol followed by heating to give heterocycles of Formula Xc. Oxidation of Xc With an appropriate oxidizing agent in a suitable medium, e.g. manganese dioxide in aqueous sodium hydroxide or potassium ferricyanide inaqueous ammomium hydroxide, affords IIh. ##STR13##

By the same technique demonstrated in Scheme 7, nitrophenyl hydrazines and nitropyridinyl hydrazines of Formula Xd (Equation 3) can be converted to heterocycles of Formula IIj which are regioisomeric with IIh. ##STR14##

Scheme 8 illustrates the preparation of benzotriazines and pyridotriazines of Formula IIh and their N-oxides IIk and IIl where R⁵ is halogen, OR⁶, or SR⁷ and R, R¹, X, and G are as previously defined. Using the conditions of Wolf et al (J. Org. Chem. 1954, 76, 3551), reaction of VIa with cyanamide in an acid medium such as a mixture of concentrated hydrochloric and acetic acid (extremely exothermic) followed by heating with aqueous base, e.g. sodium hydroxide, provides aminoheterocyclic N-oxides of Formula Xd. Diazotization with sodium nitrite in aqueous sulfuric acid gives hydroxy-heterocycles Xe and diazotization in concentrated hydrochloric acid yields chloroheterocycles IIk. By chemistry previously discussed in Scheme 3, IIl can be obtained from both Xe abd IIk. Reduction of the N-oxides IIl, e.g. catalytic hydrogenation over palladium, afford IIh. N-oxides IIl can also be coupleddirectly with III to give N-oxides of I. ##STR15##

Regioisomeric benzotriazines and pyridotriazines of Formula IIj (Equation 4) and their N-oxides where R⁵ is halogen, OR⁶, or SR⁷ and R, R¹, G, and X are as defined previously, can be obtained by starting with nitroanilines and nitropyridinylamines of Formula Xg and applying the chemistry shown in Scheme 8. ##STR16##

By the methods illustrated in Scheme 3, compounds Xe (Scheme 8) can be converted-to compounds of Formula IIl as shown in Equation 5. ##STR17##

Scheme 9 demonstrates the synthesis of heterocycles of Formula IIm and IIn (where R⁵ is haloalkyl, halocycloalkyl, haloalkenyl, or haloalkynyl and other groups defined as indicated above) from amino compounds XI and anhydrides of Formula XIa. The chemistry is related to that described in previous schemes. Hydrogenolysis e.g. catalytic using palladium on carbon,or displacement with R⁸⁻ M⁺ (where R⁸ is alkoxy, CN, or alkyl) of the chloro group of IIm affords IIn where R⁸ is hydrogen, alkoxy, CN, or alkyl. ##STR18##

Preparation of compounds of Formula IIo, IIm, and IIn where R⁵ is halogen, OR⁶ or SR⁷ and the remaining groups are as previously defined is shown in Scheme 10. The chemistry in Scheme 10 is similar to that described in previous schemes. ##STR19##

Cinnolines of Formula II where X is CH, Y is CR⁸, Z is CR⁵ and Q is N, (other substituents as previously defined) can be prepared by the methods reviewed by Elderfield (Heterocyclic Compounds, John Wiley & Sons,957, Volume 6, Chapter 5) and used in conjunction with procedures provided in the previous schemes.

N-oxides of compounds of Formula I can be made by treating compounds of Formula I with an oxidizing agent such as meta-peroxybenzoic acid in an appropriate solvent such as methylene chloride. Salts of Formula I can also be prepared by treating compounds of Formula I with a suitable acid such as hydrochloric acid.

EXAMPLE 1

Preparation of 3-(trifluoromethyl)phenyltrimethylstannane

To 20.0 g (88.9 mmol) of meta-bromobenzotrifluoride stirring in 200 ml of tetrahydrofuran at 78° C., 61.2 ml of 1.6M n-butyl lithium (97.9 mmol) in hexane was added dropwise. After stirring the reaction 10 minutesat -78° C., 19.5 g (97.8 mmol) of trimethyltin chloride dissolved in30 ml of tetrahydrofuran was added dropwise and the mixture stirred for 10 minutes at -78° C. before allowing to warm to room temperature. Thereaction mixture was quenched with excess saturated sodium bicarbonate and extracted with ethyl acetate (300 ml). The extract was washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated in vacuo to give a crude yield of 20.2 g of the above product, isolated as a oily semi-solid. This aryl stannane was used directly as a crude material in the coupling reactions with heterocycles of Formula II.

EXAMPLE 2

Preparation of 6-Methyl-2-(2,2,2-trifluoroethoxy)-8-[3-(trifluoromethyl)phenyl]quinoline

To 25.0 g (134.4 mmol) of 2-bromo-4-methylaniline stirring in 100 ml of pyridine at 0° C., 29.1 g (174.7 mmol) of cinnamoyl chloride was added dropwise. The mixture was allowed to warm to room temperature and stirred as a thick suspension for 1 h. Methylene chloride (400 ml) and excess 5% hydrochloric acid was added. The organic layer was separated, washed with 5% hydrochloric acid (2X), water and brine, dried over magnesium sulfate, and evaporated in vacuo. To the residue, n-butyl chloride was added and a solid filtered and dried to give a 33.8 g yield of N-2-bromo-4-methylphenyl cinnamide, m.p. 148°-149° C. (ethyl acetate).

A mixture of 15.0 g (47.5 mmol) of the above prepared N-2-bromo-4-methylphenyl cinnamide and 18.9 g (142.1 mmol) of aluminum trichloride was heated as a melt at about 100° C. for 1.25 h. The viscous syrup was poured onto ice and the resulting aqueous mixture stirred 10 minutes and extracted with ethyl acetate (400 ml). The organic extract was washed with water, brine, dried over magnesium sulfate, and evaporated in vacuo. To the residue was added n-butyl chloride and 5.5 g of a crude solid (8-bromo-2-hydroxy-6-methylquinoline) was filtered, dried, and taken on directly to the next step without characterization.

A 5.0 g sample of the above solid and 35 ml of phosphorous oxychloride was heated at reflux for 30 minutes. The hot mixture was poured onto excess ice and the resulting aqueous mixture extracted with 300 ml of diethyl ether. The ether extract was separated and washed with water, brine, driedover magnesium sulfate, and evaporated in vacuo to give a dark oil. Silica gel column chromatography (5:1 followed by 3:1 hexane/ethyl acetate) afforded 1.8 g of 8-bromo-2-chloro-6-methylquinoline isolated as a solid, m.p. 107°-108° C. A second lower R_(f) material (1.1 g) was also isolated on chromatography and identified as 2-chloro-6-methylquinoline, m.p. 109°-111° C.

To 0.8 g of 60% sodium hydride (oil dispersion) stirring in 20 ml of tetrahydrofuran at room temperature, 2.5 ml (34.3 mmol) of 2,2,2-trifluoroethanol was added dropwise. An exotherm occurred and to theresulting solution 1.7 g (6.7 mmol) of 8-bromo-2-chloro-6-methyl-quinoline was added followed by heating at reflux for 7 h. Ethyl acetate (200 ml) and excess water was added and the organic layer separated and washed withwater and brine, dried over magnesium sulfate, and evaporated in vacuo to give an oil. Silica gel column chromatography (20:1 followed by 10:1 hexane/ethyl acetate) afforded 1.9 g of 8-bromo-6-methyl-2-(2,2,2-trifluoroethoxy)quinoline, m.p. 61°-62° C.

A mixture of 1.5 g (6.2 mmol) of 8-bromo-6-methyl-2-(2,2,2-trifluoroethoxy)quinoline, 2.3 g of crude 3-(trifluoromethyl)phenyltrimethylstannane (Example 1), and 0.2 g of tetrakis(triphenylphosphine)palladium(O) was heated in 30 ml of toluene atreflux with stirring for 3 hours. Ethyl acetate (200 ml) and excess water was added. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo to give an oil. Silica gel column chromatography (20:1 followed by 10:1 hexane/ethyl acetate) afforded 0.7 g of product, isolated as an oil. NMR(CDCl₃): ppm 2.55 (s, 3H), 4.71 (q, 2H), 7.15 (d, 1H), 7.5-8.15 (m, 7H).

EXAMPLE 3

Preparation of 6-Methyl-2-(2,2,2-trifluoroethoxy)-8-[3-(trifluoromethyl)phenyl]quinoxaline and 6-Methyl-3-(2,2,2-trifluoroethoxy)-8-[3-(trifluoromethyl)phenyl]quinoxaline

A mixture of 22.0 g (92.2 mmol) of 2-bromo-4-methyl-6-nitroaniline and catalytic amount of 10% palladium on carbon in 120 ml of tetrahydrofuran was placed on a Paar hydrogenator for 6 h at room temperature at 50-40 psi. The reaction mixture was filtered through celite and to the filtrate was added dropwise 50.0 ml of 50% glyoxylic acid. The resulting suspensionwas stirred at room temperature overnight, the insoluble material filtered,washed with water and ethyl acetate, and oven dried to yield 8.5 g of a mixture of 8-bromo-2-hydroxy-6-methylquinoxaline and 8-bromo-3-hydroxy-6-methylquinoxaline.

A 5.0 g (20.9 mmol) sample of the above mixture of 2- and 3-hydroxyquinoxalines was heated in 30 ml of thionyl chloride containing afew drops of dimethylformamide. The reaction was heated at reflux for 1.5 hand the resulting solution, which gradually formed on heating, was poured carefully onto ice. The aqueous mixture was extracted with ethyl acetate (250 ml) and the separated organic layer washed with water (2X) and brine,dried over magnesium sulfate, and evaporated in vacuo (not to dryness) to give a wet yellow solid residue. Hexane was added and the mixture stirred several minutes before filtering to give 2.1 g of only 8-bromo-3-chloro-6-methyl-quinoxaline. Evaporating the hexane filtrate to dryness gave another 3.2 g of a crude solid which was roughly a 1:1 mixture of 8-bromo-2-chloro-6-methyl-quinoxaline and 8-bromo-3-chloro-6-methylquinoxaline.

To 0.46 g of 60% sodiumshydride (oil dispersion) stirring in 20 ml of tetrahydrofuran, was added dropwise 1.54 ml of 2,2,2-trifluoroethanol followed by the addition of 1.8 g of the above crude mixture of quinoxalines. The reaction mixture was heated at reflux 45 minutes. Glacial acetic acid (2.0 ml) and excess water was added and the aqueous mixture extracted with ethyl acetate. The separated organic layer was washed with water, saturated sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated in vacuo to give 2.4 g of an oily solid residue which was taken on directly to the next step.

A stirred mixture of 2.4 g of the above oily solid residue, 4.5 g of .crude3-(trifluoromethyl)phenyltrimethylstannane (Example 1), and 0.2 g of tetrakis (triphenylphosphine) palladium(0) was heated in 30 ml of toluene for 4 h. The reaction mixture was concentrated to dryness in vacuo and theresidue flash chromatographed on silica gel (40:1 hexane/ethyl acetate) to give 0.7 g of 6-methyl-3-(2,2,2-trifluoroethoxy)-8-[3-(trifluoromethyl)phenyl]quinoxaline (first to elute, m.p. 114°-117° C.) and 0.8 g of 6-methyl-2-(2,2,2-trifluoroethoxy)-8-[3-(trifluoromethyl)phenyl]-quinoxaline (m.p. 46°-48° C.).

EXAMPLE 4

Preparation of 2-Methoxy-6-methyl-8-[3-(trifluoromethyl)phenyl]quinoxaline and 3-Methoxy-6-methyl-8-[3-(trifluoromethyl)phenyl]quinoxaline

To 2.3 g of a crude sample mixture of 8-bromo-2-chloro-6-methylquinoxaline and 8-bromo-3-chloro-6-methylquinoxaline (prepared as in Example 3) stirring in 20 ml of methanol, 6.3 ml of a 25 weight % of sodium methoxidein methanol was added and the mixture heated at reflux for 1 h. Glacial acetic acid (3.0 ml), 200 ml of ethyl acetate, and excess water was added.The separated organic layer was washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate, and evaporated in vacuo to give 2.0 gof an oily solid residue which was taken on directly to the next step.

A stirred mixture of the above oily solid residue, 3.2 g of crude 3-(trifluoromethyl)phenyltrimethylstannane (Example 1), and 0.2 g of tetrakis(triphenylphosphine)palladium(0) were heated in 35 ml of toluene at reflux for 8 h. In vacuo, the reaction mixture was evaporated to dryness and the residue flash chromatographed on silica gel (1:1 hexane/n-butyl chloride followed by straight n-butyl chloride) to give 0.4g of 3-methoxy-5-methyl-8-[3-(trifluoromethyl)phenyl]quinoxaline (first product isomer to elute, m.p. 141°-142° C.) and 0.5 g of 2-methoxy-5-methyl-8-[3-(trifluoromethyl)phenyl]quinoxaline (m.p. 119°-121° C.).

EXAMPLE 5

Preparation of 2-(Difluoromethoxy)-6-methyl-8-[3-(trifluoromethyl)phenyl]quinoxaline and 3-(Difluoromethoxy)-6-methyl-8-[3-(trifluoromethyl)phenyl]quinoxaline

To a suspension of 5.0 g (20.9 mmol) of the above isomer mixture of 8-bromo-2-hydroxy-6-methylquinoxaline and 8-bromo-3-hydroxy-6-methylquinoxaline (prepared as in Example 3) and 9.0 g(27.1 mmol) of tetra-n-butylammonium bromide stirring in 150 ml of dioxane,20 g (250.0 mmol) of 50% aqueous sodium hydroxide were added. The reaction mixture was placed under an atmosphere of chlorodifluoromethane (Freon22*)whereby slight pressure was maintained by having a balloon over the reaction flask. A slow exotherm occurred and the mixture stirred 4 h. Excess water and 300 ml of diethyl ether were added. The separated organicextract was washed with water, brine, dried over magnesium sulfate, and evaporated in vacuo to give an oil residue which quickly solidified. Hexane was added, the mixture stirred several minutes, and filtered to give 3.1 g of 8-bromo-3-difluoromethoxy-6-methylquinoxaline. Evaporating the filtrate gave 2.5 g of a crude isomer mixture of 8-bromo-2-difluoromethoxy-6-methylquinoxaline and 8-bromo-3-difluoromethoxy-6-methylquinoxaline.

A stirred mixture of 1.5 g (5.2 mmol) of the above 2- and 3-difluoromethoxyquinoxaline isomer mixture, 4.0 g of crude 3-(trifluoromethyl)phenyltrimethylstannane (Example 1), and 0.2 g of tetrakis(triphenylphosphine)palladium(0) was heated at reflux for 16 h. The reaction mixture was evaporated in vacuo and the residue flash chromatographed on silica gel (9:1 followed by 1:1 hexane/n-butyl chloride) to afford 0.51 g of 3-(difluoromethoxy)-6-methyl-8-[3-(trifluoromethyl)phenyl]quinoxaline (first product isomer to elute, m.p. 105°-106° C.) and 0.4 gof 2-(difluoromethoxy)-6-methyl-8-[3-(trifluoromethyl)phenyl]quinoxaline (m.p. 103°-104° C.).

EXAMPLE 6

Preparation of 6-Methyl-2-(trifluoromethyl)-8-[3-(trifluoromethyl)phenyl]quinoxaline and 6-Methyl-3-(trifluoromethyl)-8-[3-(trifluoromethyl)phenyl]quinoxaline

A mixture of 2 0.0 g (86.6 mmol) of 2-bromo-4-methyl-6-nitroaniline and a catalytic amount of 10% palladium on carbon in 100 ml of tetrahydrofuran was placed on a Paar hydrogenator at room temperature at 50-40 psi for 6 h. The reaction mixture was filtered through celite which was then washed with ethyl acetate. A total of 300 ml of ethyl acetate was added to the filtrate which was washed with water, brine, dried over magnesium sulfate and evaporated in vacuo to give a dark oily semi-solid. Flash column silica gel chromatography (methylene chloride followed by 2:1 hexane/ethylacetate) afforded 17.0 g of the main component: 3-bromo-5-methyl-ortho-phenylenediamine. The chromatopgraphed product, which still contained some minor impurities, was used directly in the nextstep. It was initially an dark oil which solidified.

To 10.0 g (37.0 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone stirring in 50 ml of water, 8.0 g (97.6 mmol) of anhydrous sodium acetate was added and the stirred mixture heated near reflux for 45 minutes followed by stirringat ambient temperature for 30 minutes. A 4.0 g (20.0 mmol) sample of the above phenylenediamine was added and the mixture stirred 2 h. Excess waterand 250 ml of ethyl acetate was added and the separated organic extract washed with 5% hydrochloric acid, brine, dried over magnesium sulfate, andevaporated in vacuo to give dark oil. Flash column silica gel chromatography (40:1 followed by 30:1 hexane/ethyl acetate) afforded 4.3 gof a mixture (two close migrating spots) of 8-bromo-6-methyl-2-trifluoromethylquinoxaline and 8-bromo-6-methyl-3-trifluoromethylquinoxaline, isolated as a solid which melted at 69°-71° C.

A stirred mixture of 2.0 g (6.9 mmol) of the above quinoxaline isomers, 4.2g of crude 3-(trifluoromethyl)phenyltrimethylstannane, and 0.2 g of tetrakis(triphenylphosphine)palladium(0) were heated in 30 ml of toluene for 6 h. Additional stannane (about 0.5 g) and palladium catalyst (0.1 g) were added and the reaction heated another 6 h. The reaction mixture was evaporated in vacuo to dryness and the residue flash chromatographed (4:1 followed by 1:1 hexane/n-butyl chloride followed in turn by 100% n-butyl chloride) to afford 0.2 g of 6-methyl-3-(trifluoromethyl)-8-[3-(trifluoromethyl)-phenyl]quinoxaline (first product isomer to elute, m.p. 93°-94° C.) and 1.08 g of 6-methyl-2-(trifluoro-methyl)-8-[3-(trifluoromethyl)phenyl]-quinoxaline(m.p. 117°-118° C.).

EXAMPLE 7

7-Methyl-3-(2,2,2-trifluoroethoxy)-5-[3-(trifluoromethyl)phenyl]-1,2,4-benzotriazine-1-oxide and 7-Methyl-3-(2,2,2-trifluoroethoxy)-5-[3-(trifluoromethyl)phenyl]-1,2,4-benzotriazine

To 13.0 g (56.3 mmol) of 2-bromo-4-methyl-6-nitroaniline stirring in a mixture of 25 ml glacial acetic acid and 5 ml of concentrated hydrochloricacid at 80° C., 29.0 g (690.5 mmol) of cyanamide and 25 ml of concentrated hydrochloric acid were added simultaneously, separately, and very slowly. At one point during the addition, a vigorous exotherm occurred and the external heat immediately removed. After the addition, the reaction was heated at reflux for 15 minutes. On cooling to about 50° C., 100 ml of 25% aqueous sodium hydroxide were added dropwise and the mixture heated at reflux 15 minutes. The reaction was cooled to room temperature, the insoluble orange solid filtered and washed with water followed by ethyl acetate to afford 7.4 g of yellow 3-amino-5-bromo-7-methyl-1,2,4-benzotriazine-1-oxide after drying.

Sodium nitrite (7.0 g, 101.4 mmol) was added portionwise to a suspension of7.0 g (27.5 mmol) of the above aminobenzotriazine-N-oxide stirring in 140 ml of concentrated hydrochloric acid at ambient temperature. The mixture was stirred overnight and heated at 60° C. for 2 h. Excess water and 400 ml of ethyl acetate were added and the separated organic layer washed with water, saturated sodium bicarbonate, brine, and dried over magnesium sulfate. Some insoluble starting aminoheterocycle was present during the extractive workup but was not attempted to be removed. Evaporating the organic extract to dryness in vacuo afforded a crude yellow solid residue which was flash chromatographed on silica gel (4:1 methylene chloride/hexane) to give 2.5 g of 5-bromo-3-chloro-7-methyl-1,2,4-benzotriazine-1-oxide, m.p. 207°-209° C.

To 0.5 g of 60% sodium hydride stirring in 30 ml of tetrahydrofuran, 3.0 mlof 2,2,2-trifluoroethanol was added dropwise at ambient temperature. A solution resulted and 2.0 g (7.29 mmol) of the above 5-bromo-3-chloro-7-methyl-1,2,4-benzotriazine-1-oxide was added and at ambient temperature and the mixture stirred 2 h. Ethyl acetate (200 ml) and excess water were added and the separated organic extract washed with water, brine, and dried over magnesium sulfate. The solvent was removed invacuo, hexane added to the residue, and the suspended yellow s 61id filtered and dried to afford 1.7 g of 5-bromo-7-methyl-3-(2,2,2-trifluoroethoxy) -1,2,4-benzotriazine-1-oxide, m.p. 127°-128° C.

A stirred mixture of 1.3 g (3.84 mmol) of the above benzotriazine N-oxide, 1.4 g of crude 3-(trifluoromethyl)phenyltrimethylstannane, and 0.2 g of tetrakis(triphenylphosphine)palladium(0) were heated in 35 ml of toluene at reflux for 4 h. The reaction mixture was evaporated in vacuo to drynessand the residue flashed chromatographed on silica gel (1:1 hexane/n-butyl chloride followed by 100% n-butyl chloride) to give 0.8 g of 7-methyl-3-(2,2,2-trifluoroethoxy)-5-[3-(trifluoromethyl)phenyl]-1,2,4-benzotriazine-1-oxide (m.p. 168°-169° C.) and 0.24 g of 7-methyl-3-(2,2,2-trifluoroethoxy)-5-[3-(trifluoromethyl)phenyl]-1,2,4-benzotriazine (m.p. 140°-141°).

Using the procedures outlined in Schemes 1-10, Equations 1-5, and Examples 1-7, the compounds of Tables I-VIII and the Table of Compounds can readilybe prepared by one skilled in the art.

                                      TABLE I                                      __________________________________________________________________________      ##STR20##                                                                     X  R       R.sup.1                                                                          R.sup.2                                                                             R.sup.3                                                                             R.sup.4                                                                            R.sup.5 R.sup.8                                     __________________________________________________________________________     CH Me      H H    CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH Et      H H    CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH n-Pr    H H    CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH Me      H H    OCF.sub.3                                                                           H   CF.sub.3                                                                               H                                           CH Et      H H    OCF.sub.3                                                                           H   CF.sub.3                                                                               H                                           CH n-Pr    H H    OCF.sub.3                                                                           H   CF.sub.3                                                                               H                                           CH Me      H H    OCHF.sub.2                                                                          H   CF.sub.3                                                                               H                                           CH Me      H H    OCF.sub.3                                                                           H   OCHF.sub.2                                                                             H                                           CH Me      H H    CF.sub.3                                                                            H   OCHF.sub.2                                                                             H                                           CH Me      F H    CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH Me      H 6-F  CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH Me      H 4-F  CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH Me      H 2-OMe                                                                               CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH Me      H 2-CF.sub.3                                                                          H    H   CF.sub.3                                                                               H                                           CH Me      H H    Cl   H   CF.sub.3                                                                               H                                           CH Me      H H    Br   H   CF.sub.3                                                                               H                                           CH Me      H H    CN   H   CF.sub.3                                                                               H                                           CH Et      H H    CF.sub.3                                                                            H   OCHF.sub.2                                                                             H                                           CH Et      H H    CN   H   CF.sub.3                                                                               H                                           CH Me      H H    SCF.sub.3                                                                           H   CF.sub.3                                                                               H                                           CH Me      H H    H    H   CF.sub.3                                                                               H                                           CH Me      H H    CF.sub.3                                                                            H   OCH.sub.2 CF.sub.3                                                                     H                                           CH Me      H H    CF.sub.3                                                                            H   SCF.sub.3                                                                              H                                           CH Me      H H    CF.sub.3                                                                            H   OMe     H                                           CH Et      H H    CF.sub.3                                                                            H   OEt     H                                           CH Me      H H    CF.sub.3                                                                            H   OCHMe.sub.2                                                                            H                                           CH Me      H H    CF.sub.3                                                                            H   SMe     H                                           CH Me      H H    CF.sub.3                                                                            H   CHF.sub.2                                                                              H                                           CH Et      H H    CF.sub.3                                                                            H   CHF.sub.2                                                                              H                                           CH Me      H H    OCF.sub. 3                                                                          H   CHF.sub.2                                                                              H                                           CH Me      H H    CF.sub.3                                                                            H   OCF.sub.2 CHF.sub.2                                                                    H                                           CH Me      H H    CF.sub.3                                                                            H   Cl      H                                           CH MeCHCH  H H    CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH Me      H H    CF.sub.3                                                                            H   CHCHCF.sub.3                                                                           H                                           CH Me      H H    CF.sub.3                                                                            H   OCHF.sub.2                                                                             H                                           CH Et      H H    CF.sub.3                                                                            H   OCHF.sub.2                                                                             H                                           CH MeOCH.sub.2                                                                            H H    CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH Me.sub.2 N                                                                             H H    CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH MeNH    H H    CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH Me      H H    OMe  H   CF.sub.3                                                                               H                                           CH Me      H H    CF.sub.3                                                                            H   SCHF.sub.2                                                                             H                                           CH Me      H H    CF.sub.3                                                                            H   SO.sub.2 CHF.sub.2                                                                     H                                           CH MeO     H H    CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH MeS     H H    CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           CH Me      H H    CF.sub.3                                                                            Me  CF.sub.3                                                                               H                                           CH Me      H H    CF.sub.3                                                                            CN  CF.sub.3                                                                               H                                           CH Me      H H    CF.sub.3                                                                            OMe CF.sub.3                                                                               H                                           CH Me      H H    CF.sub.3                                                                            Cl  CF.sub.3                                                                               H                                           N  Me      H H    CF.sub.3                                                                            H   CF.sub. 3                                                                              H                                           N  Et      H H    CF.sub.3                                                                            H   CF.sub.3                                                                               H                                           N  Me      H H    CF.sub.3                                                                            H   OCHF.sub.2                                                                             H                                           N  Et      H H    CF.sub.3                                                                            H   OCHF.sub.2                                                                             H                                           N  Me      H H    OCF.sub.3                                                                           H   CF.sub.3                                                                               H                                           N  Me      H H    OCHF.sub.2                                                                          H   CF.sub.3                                                                               H                                           N  Me      H H    CN   H   CF.sub.3                                                                               H                                           N  Et      H H    CN   H   CF.sub.3                                                                               H                                           N  Me      H H    OCF.sub.3                                                                           H   OCHF.sub.2                                                                             H                                           N  Me      H H    CF.sub.3                                                                            H   OMe     H                                           N  Me      H H    SCF.sub.3                                                                           H   CF.sub.3                                                                               H                                           CH Me      H H    CF.sub.3                                                                            H   CF.sub.3                                                                               Me                                          CH Me      H H    CF.sub.3                                                                            H   CF.sub.3                                                                               OMe                                         CH Me      H H    CF.sub.3                                                                            H   CF.sub.3                                                                               Cl                                          CH Me      H H    CF.sub.3                                                                            H   CF.sub.3                                                                               CN                                          __________________________________________________________________________

                                      TABLE II                                     __________________________________________________________________________      ##STR21##                                                                     X  R       R.sup.1                                                                          R.sup.2                                                                              R.sup.3                                                                             R.sup.4                                                                            R.sup.5                                                                               R.sup.8                                     __________________________________________________________________________     CH Me      H H     CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH Et      H H     CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH n-Pr    H H     CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH Me      H H     OCF.sub.3                                                                           H   CF.sub.3                                                                              H                                           CH Et      H H     OCF.sub.3                                                                           H   CF.sub.3                                                                              H                                           CH n-Pr    H H     OCF.sub.3                                                                           H   CF.sub.3                                                                              H                                           CH Me      H H     OCHF.sub.2                                                                          H   CF.sub.3                                                                              H                                           CH Me      H H     OCF.sub.3                                                                           H   OCHF.sub.2                                                                            H                                           CH Me      H H     CF.sub.3                                                                            H   OCHF.sub.2                                                                            H                                           CH Me      F H     CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH Me      H 6-F   CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH Me      H 4-F   CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH Me      H 2-OMe CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH Me      H 2-CF.sub.3                                                                           H    H   CF.sub.3                                                                              H                                           CH Me      H H     Cl   H   CF.sub.3                                                                              H                                           CH Me      H H     Br   H   CF.sub.3                                                                              H                                           CH Et      H H     CF.sub.3                                                                            H   OCHF.sub.2                                                                            H                                           CH Me      H H     CN   H   CF.sub.3                                                                              H                                           CH Et      H H     CN   H   CF.sub.3                                                                              H                                           CH Me      H H     SCF.sub.3                                                                           H   CF.sub.3                                                                              H                                           CH Me      H H     H    H   CF.sub.3                                                                              H                                           CH Me      H H     CF.sub.3                                                                            H   OCH.sub.2 CF.sub.3                                                                    H                                           CH Me      H H     CF.sub.3                                                                            H   SCF.sub.3                                                                             H                                           CH Me      H H     CF.sub.3                                                                            H   OMe    H                                           CH Et      H H     CF.sub.3                                                                            H   OEt    H                                           CH Me      H H     CF.sub.3                                                                            H   OCHMe.sub.2                                                                           H                                           CH Me      H H     CF.sub.3                                                                            H   SMe    H                                           CH Me      H H     CF.sub.3                                                                            H   CHF.sub.2                                                                             H                                           CH Et      H H     CF.sub.3                                                                            H   CHF.sub.2                                                                             H                                           CH Me      H H     OCF.sub. 3                                                                          H   CHF.sub.2                                                                             H                                           CH Me      H H     CF.sub.3                                                                            H   OCF.sub.2 CHF.sub.2                                                                   H                                           CH Me      H H     CF.sub.3                                                                            H   Cl     H                                           CH MeCHCH  H H     CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH Me      H H     CF.sub.3                                                                            H   CHCHCF.sub.3                                                                          H                                           CH Me      H H     CF.sub.3                                                                            H   OCHF.sub.2                                                                            H                                           CH Et      H H     CF.sub.3                                                                            H   OCHF.sub.2                                                                            H                                           CH MeOCH.sub.2                                                                            H H     CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH Me.sub.2 N                                                                             H H     CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH MeNH    H H     CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH Me      H H     OMe  H   CF.sub.3                                                                              H                                           CH Me      H H     CF.sub.3                                                                            H   SCHF.sub.2                                                                            H                                           CH Me      H H     CF.sub.3                                                                            H   SO.sub.2 CHF.sub.2                                                                    H                                           CH MeO     H H     CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH MeS     H H     CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           CH Me      H H     CF.sub.3                                                                            Me  CF.sub.3                                                                              H                                           CH Me      H H     CF.sub.3                                                                            CN  CF.sub.3                                                                              H                                           CH Me      H H     CF.sub.3                                                                            OMe CF.sub.3                                                                              H                                           CH Me      H H     CF.sub.3                                                                            Cl  CF.sub.3                                                                              H                                           N  Me      H H     CF.sub.3                                                                            H   CF.sub. 3                                                                             H                                           N  Et      H H     CF.sub.3                                                                            H   CF.sub.3                                                                              H                                           N  Me      H H     CF.sub.3                                                                            H   OCHF.sub.2                                                                            H                                           N  Et      H H     CF.sub.3                                                                            H   OCHF.sub.2                                                                            H                                           N  Me      H H     OCF.sub.3                                                                           H   CF.sub.3                                                                              H                                           N  Me      H H     OCHF.sub.2                                                                          H   CF.sub.3                                                                              H                                           N  Me      H H     CN   H   CF.sub.3                                                                              H                                           N  Et      H H     CN   H   CF.sub.3                                                                              H                                           N  Me      H H     OCF.sub.3                                                                           H   OCHF.sub.2                                                                            H                                           N  Me      H H     CF.sub.3                                                                            H   OMe    H                                           N  Me      H H     SCF.sub.3                                                                           H   CF.sub.3                                                                              H                                           CH Me      H H     CF.sub.3                                                                            H   CF.sub.3                                                                              Me                                          CH Me      H H     CF.sub.3                                                                            H   CF.sub.3                                                                              OMe                                         CH Me      H H     CF.sub.3                                                                            H   CF.sub.3                                                                              Cl                                          CH Me      H H     CF.sub.3                                                                            H   CF.sub.3                                                                              CN                                          __________________________________________________________________________

                  TABLE III                                                        ______________________________________                                          ##STR22##                                                                     X    R          R.sup.1                                                                              R.sup.2                                                                              R.sup.3                                                                               R.sup.4                                                                             R.sup.5                                ______________________________________                                         CH   Me         H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Et         H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   n-Pr       H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     H     OCF.sub.3                                                                             H    CF.sub.3                               CH   Et         H     H     OCF.sub.3                                                                             H    CF.sub.3                               CH   n-Pr       H     H     OCF.sub.3                                                                             H    CF.sub.3                               CH   Me         H     H     OCHF.sub.2                                                                            H    CF.sub.3                               CH   Me         H     H     OCF.sub.3                                                                             H    OCHF.sub.2                             CH   Me         H     H     CF.sub.3                                                                              H    OCHF.sub.2                             CH   Me         F     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     6-F   CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     4-F   CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     2-OMe CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     2-CF.sub.3                                                                           H      H    CF.sub.3                               CH   Me         H     H     Cl     H    CF.sub.3                               CH   Et         H     H     CF.sub.3                                                                              H    OCHF.sub.2                             CH   Me         H     H     Br     H    CF.sub.3                               CH   Me         H     H     CN     H    CF.sub.3                               CH   Et         H     H     CN     H    CF.sub.3                               CH   Me         H     H     SCF.sub.3                                                                             H    CF.sub.3                               CH   Me         H     H     H      H    CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              H    OCH.sub.2 CF.sub.3                     CH   Me         H     H     CF.sub.3                                                                              H    SCF.sub.3                              CH   Me         H     H     CF.sub.3                                                                              H    OMe                                    CH   Et         H     H     CF.sub.3                                                                              H    OEt                                    CH   Me         H     H     CF.sub.3                                                                              H    OCHMe.sub.2                            CH   Me         H     H     CF.sub.3                                                                              H    SMe                                    CH   Me         H     H     CF.sub.3                                                                              H    CHF.sub.2                              CH   Et         H     H     CF.sub.3                                                                              H    CHF.sub.2                              CH   Me         H     H     OCF.sub.3                                                                             H    CHF.sub.2                              CH   Me         H     H     CF.sub.3                                                                              H    OCF.sub.2 CHF.sub.2                    CH   Me         H     H     CF.sub.3                                                                              H    Cl                                     CH   MeCHCH     H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              H    CHCHCF.sub.3                           CH   Me         H     H     CF.sub.3                                                                              H    OCHF.sub.2                             CH   Et         H     H     CF.sub.3                                                                              H    OCHF.sub.2                             CH   MeOCH.sub.2                                                                               H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Me.sub.2 N H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   MeNH       H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     H     OMe    H    CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              H    SCHF.sub.2                             CH   Me         H     H     CF.sub.3                                                                              H    SO.sub.2 CHF.sub.2                     CH   MeO        H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   MeS        H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              Me   CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              CN   CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              OMe  CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              Cl   CF.sub.3                               N    Me         H     H     CF.sub.3                                                                              H    CF.sub.3                               N    Et         H     H     CF.sub.3                                                                              H    CF.sub.3                               N    Me         H     H     CF.sub.3                                                                              H    OCHF.sub.2                             N    Et         H     H     CF.sub.3                                                                              H    OCHF.sub.2                             N    Me         H     H     OCF.sub.3                                                                             H    CF.sub.3                               N    Me         H     H     OCHF.sub.2                                                                            H    CF.sub.3                               N    Me         H     H     CN     H    CF.sub.3                               N    Et         H     H     CN     H    CF.sub.3                               N    Me         H     H     OCF.sub.3                                                                             H    OCHF.sub.2                             N    Me         H     H     CF.sub.3                                                                              H    OMe                                    N    Me         H     H     SCF.sub.3                                                                             H    CF.sub.3                               ______________________________________                                    

                  TABLE IV                                                         ______________________________________                                          ##STR23##                                                                     X    R          R.sup.1                                                                              R.sup.2                                                                              R.sup.3                                                                               R.sup.4                                                                             R.sup.5                                ______________________________________                                         CH   Me         H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Et         H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   n-Pr       H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     H     OCF.sub.3                                                                             H    CF.sub.3                               CH   Et         H     H     OCF.sub.3                                                                             H    CF.sub.3                               CH   n-Pr       H     H     OCF.sub.3                                                                             H    CF.sub.3                               CH   Me         H     H     OCHF.sub.2                                                                            H    CF.sub.3                               CH   Me         H     H     OCF.sub.3                                                                             H    OCHF.sub.2                             CH   Me         H     H     CF.sub.3                                                                              H    OCHF.sub.2                             CH   Me         F     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     6-F   CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     4-F   CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     2-OMe CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     2-CF.sub.3                                                                           H      H    CF.sub.3                               CH   Me         H     H     Cl     H    CF.sub.3                               CH   Me         H     H     Br     H    CF.sub.3                               CH   Et         H     H     CF.sub.3                                                                              H    OCHF.sub.2                             CH   Me         H     H     CN     H    CF.sub.3                               CH   Et         H     H     CN     H    CF.sub.3                               CH   Me         H     H     SCF.sub.3                                                                             H    CF.sub.3                               CH   Me         H     H     H      H    CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              H    OCH.sub.2 CF.sub.3                     CH   Me         H     H     CF.sub.3                                                                              H    SCF.sub.3                              CH   Me         H     H     CF.sub.3                                                                              H    OMe                                    CH   Et         H     H     CF.sub.3                                                                              H    OEt                                    CH   Me         H     H     CF.sub.3                                                                              H    OCHMe.sub.2                            CH   Me         H     H     CF.sub.3                                                                              H    SMe                                    CH   Me         H     H     CF.sub.3                                                                              H    CHF.sub.2                              CH   Et         H     H     CF.sub.3                                                                              H    CHF.sub.2                              CH   Me         H     H     OCF.sub.3                                                                             H    CHF.sub.2                              CH   Me         H     H     CF.sub.3                                                                              H    OCF.sub.2 CHF.sub.2                    CH   Me         H     H     CF.sub.3                                                                              H    Cl                                     CH   MeCHCH     H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              H    CHCHCF.sub.3                           CH   Me         H     H     CF.sub.3                                                                              H    OCHF.sub.2                             CH   Et         H     H     CF.sub.3                                                                              H    OCHF.sub.2                             CH   MeOCH.sub.2                                                                               H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Me.sub.2 N H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   MeNH       H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     H     OMe    H    CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              H    SCHF.sub.2                             CH   Me         H     H     CF.sub.3                                                                              H    SO.sub.2 CHF.sub.2                     CH   MeO        H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   MeS        H     H     CF.sub.3                                                                              H    CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              Me   CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              CN   CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              OMe  CF.sub.3                               CH   Me         H     H     CF.sub.3                                                                              Cl   CF.sub.3                               N    Me         H     H     CF.sub.3                                                                              H    CF.sub.3                               N    Et         H     H     CF.sub.3                                                                              H    CF.sub.3                               N    Me         H     H     CF.sub.3                                                                              H    OCHF.sub.2                             N    Et         H     H     CF.sub.3                                                                              H    OCHF.sub.2                             N    Me         H     H     OCF.sub.3                                                                             H    CF.sub.3                               N    Me         H     H     OCHF.sub.2                                                                            H    CF.sub.3                               N    Me         H     H     CN     H    CF.sub.3                               N    Et         H     H     CN     H    CF.sub.3                               N    Me         H     H     OCF.sub.3                                                                             H    OCHF.sub.2                             N    Me         H     H     CF.sub.3                                                                              H    OMe                                    N    Me         H     H     SCF.sub.3                                                                             H    CF.sub.3                               ______________________________________                                    

                  TABLE V                                                          ______________________________________                                          ##STR24##                                                                     X     R          R.sup.1                                                                               R.sup.2                                                                              R.sup.3 R.sup.5                                  ______________________________________                                         CH    Me         H      H     CF.sub.3                                                                               CF.sub.3                                 CH    Et         H      H     CF.sub.3                                                                               CF.sub.3                                 CH    n-Pr       H      H     CF.sub.3                                                                               CF.sub.3                                 CH    Me         H      H     OCF.sub.3                                                                              CF.sub.3                                 CH    Et         H      H     OCF.sub.3                                                                              CF.sub.3                                 CH    n-Pr       H      H     OCF.sub.3                                                                              CF.sub.3                                 CH    Me         H      H     OCHF.sub.2                                                                             CF.sub.3                                 CH    Me         H      H     OCF.sub.3                                                                              OCHF.sub.2                               CH    Me         H      H     CF.sub.3                                                                               OCHF.sub.2                               CH    Me         F      H     CF.sub.3                                                                               CF.sub.3                                 CH    Me         H      6-F   CF.sub.3                                                                               CF.sub.3                                 CH    Me         H      4-F   CF.sub. 3                                                                              CF.sub.3                                 CH    Me         H      2-OMe CF.sub.3                                                                               CF.sub.3                                 CH    Me         H      2-CF.sub.3                                                                           H       CF.sub.3                                 CH    Me         H      H     Cl      CF.sub.3                                 CH    Et         H      H     CF.sub.3                                                                               OCHF.sub.2                               CH    Me         H      H     Br      CF.sub.3                                 CH    Me         H      H     CN      CF.sub.3                                 CH    Et         H      H     CN      CF.sub.3                                 CH    Me         H      H     SCF.sub.3                                                                              CF.sub.3                                 CH    Me         H      H     H       CF.sub.3                                 CH    Me         H      H     CF.sub.3                                                                               OCH.sub.2 CF.sub.3                       CH    Me         H      H     CF.sub.3                                                                               SCF.sub.3                                CH    Me         H      H     CF.sub.3                                                                               OMe                                      CH    Et         H      H     CF.sub.3                                                                               OEt                                      CH    Me         H      H     CF.sub.3                                                                               OCHMe.sub.2                              CH    Me         H      H     CF.sub.3                                                                               SMe                                      CH    Me         H      H     CF.sub.3                                                                               CHF.sub.2                                CH    Et         H      H     CF.sub.3                                                                               CHF.sub.2                                CH    Me         H      H     OCF.sub.3                                                                              CHF.sub.2                                CH    Me         H      H     CF.sub.3                                                                               OCF.sub.2 CHF.sub.2                      CH    Me         H      H     CF.sub.3                                                                               Cl                                       CH    MeCHCH     H      H     CF.sub.3                                                                               CF.sub.3                                 CH    Me         H      H     CF.sub.3                                                                               CHCHCF.sub.3                             CH    Me         H      H     CF.sub.3                                                                               OCHF.sub.2                               CH    Et         H      H     CF.sub.3                                                                               OCHF.sub.2                               CH    MeOCH.sub.2                                                                               H      H     CF.sub.3                                                                               CF.sub. 3                                CH    Me.sub.2 N H      H     CF.sub.3                                                                               CF.sub.3                                 CH    MeNH       H      H     CF.sub.3                                                                               CF.sub.3                                 CH    Me         H      H     OMe     CF.sub.3                                 CH    Me         H      H     CF.sub.3                                                                               SCHF.sub.2                               CH    Me         H      H     CF.sub.3                                                                               SO.sub.2 CHF.sub.2                       CH    MeO        H      H     CF.sub.3                                                                               CF.sub.3                                 CH    MeS        H      H     CF.sub.3                                                                               CF.sub.3                                 N     Me         H      H     CF.sub.3                                                                               CF.sub.3                                 N     Et         H      H     CF.sub.3                                                                               CF.sub.3                                 N     Me         H      H     CF.sub.3                                                                               OCHF.sub.2                               N     Et         H      H     CF.sub.3                                                                               OCHF.sub.2                               N     Me         H      H     OCF.sub.3                                                                              CF.sub.3                                 N     Me         H      H     OCHF.sub.2                                                                             CF.sub.3                                 N     Me         H      H     CN      CF.sub.3                                 N     Et         H      H     CN      CF.sub.3                                 N     Me         H      H     OCF.sub.3                                                                              OCHF.sub.2                               N     Me         H      H     CF.sub.3                                                                               OMe                                      N     Me         H      H     SCF.sub.3                                                                              CF.sub.3                                 ______________________________________                                    

                  TABLE VI                                                         ______________________________________                                          ##STR25##                                                                     X     R          R.sup.1                                                                               R.sup.2                                                                              R.sup.3 R.sup.5                                  ______________________________________                                         CH    Me         H      H     CF.sub.3                                                                               CF.sub.3                                 CH    Et         H      H     CF.sub.3                                                                               CF.sub.3                                 CH    n-Pr       H      H     CF.sub.3                                                                               CF.sub.3                                 CH    Me         H      H     OCF.sub.3                                                                              CF.sub.3                                 CH    Et         H      H     OCF.sub.3                                                                              CF.sub.3                                 CH    n-Pr       H      H     OCF.sub.3                                                                              CF.sub.3                                 CH    Me         H      H     OCHF.sub.2                                                                             CF.sub.3                                 CH    Me         H      H     OCF.sub.3                                                                              OCHF.sub.2                               CH    Me         H      H     CF.sub.3                                                                               OCHF.sub.2                               CH    Me         F      H     CF.sub.3                                                                               CF.sub.3                                 CH    Me         H      6-F   CF.sub.3                                                                               CF.sub.3                                 CH    Me         H      4-F   CF.sub.3                                                                               CF.sub. 3                                CH    Me         H      2-OMe CF.sub.3                                                                               CF.sub.3                                 CH    Me         H      2-CF.sub.3                                                                           H       CF.sub.3                                 CH    Me         H      H     Cl      CF.sub.3                                 CH    Et         H      H     CF.sub.3                                                                               OCHF.sub.2                               CH    Me         H      H     Br      CF.sub.3                                 CH    Me         H      H     CN      CF.sub.3                                 CH    Et         H      H     CN      CF.sub.3                                 CH    Me         H      H     SCF.sub.3                                                                              CF.sub.3                                 CH    Me         H      H     H       CF.sub.3                                 CH    Me         H      H     CF.sub.3                                                                               OCH.sub.2 CF.sub.3                       CH    Me         H      H     CF.sub.3                                                                               SCF.sub.3                                CH    Me         H      H     CF.sub.3                                                                               OMe                                      CH    Et         H      H     CF.sub.3                                                                               OEt                                      CH    Me         H      H     CF.sub.3                                                                               OCHMe.sub.2                              CH    Me         H      H     CF.sub.3                                                                               SMe                                      CH    Me         H      H     CF.sub.3                                                                               CHF.sub.2                                CH    Et         H      H     CF.sub.3                                                                               CHF.sub.2                                CH    Me         H      H     OCF.sub.3                                                                              CHF.sub.2                                CH    Me         H      H     CF.sub.3                                                                               OCF.sub.2 CHF.sub.2                      CH    Me         H      H     CF.sub.3                                                                               Cl                                       CH    MeCHCH     H      H     CF.sub.3                                                                               CF.sub.3                                 CH    Me         H      H     CF.sub.3                                                                               CHCHCF.sub.3                             CH    Me         H      H     CF.sub.3                                                                               OCHF.sub.2                               CH    Et         H      H     CF.sub.3                                                                               OCHF.sub.2                               CH    MeOCH.sub.2                                                                               H      H     CF.sub.3                                                                               CF.sub.3                                 CH    Me.sub.2 N H      H     CF.sub.3                                                                               CF.sub.3                                 CH    MeNH       H      H     CF.sub.3                                                                               CF.sub.3                                 CH    Me         H      H     OMe     CF.sub.3                                 CH    Me         H      H     CF.sub.3                                                                               SCHF.sub.2                               CH    Me         H      H     CF.sub.3                                                                               SO.sub.2 CHF.sub.2                       CH    MeO        H      H     CF.sub.3                                                                               CF.sub.3                                 CH    MeS        H      H     CF.sub.3                                                                               CF.sub.3                                 N     Me         H      H     CF.sub.3                                                                               CF.sub.3                                 N     Et         H      H     CF.sub.3                                                                               CF.sub.3                                 N     Me         H      H     CF.sub.3                                                                               OCHF.sub.2                               N     Et         H      H     CF.sub.3                                                                               OCHF.sub.2                               N     Me         H      H     OCF.sub.3                                                                              CF.sub.3                                 N     Me         H      H     OCHF.sub.2                                                                             CF.sub.3                                 N     Me         H      H     CN      CF.sub.3                                 N     Et         H      H     CN      CF.sub.3                                 N     Me         H      H     OCF.sub.3                                                                              OCHF.sub.2                               N     Me         H      H     CF.sub.3                                                                               OMe                                      N     Me         H      H     SCF.sub.3                                                                              CF.sub.3                                 ______________________________________                                    

                  TABLE VII                                                        ______________________________________                                          ##STR26##                                                                     X    R          R.sup.1                                                                              R.sup.2                                                                              R.sup.3                                                                               R.sup.5  R.sup.8                            ______________________________________                                         CH   Me         H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Et         H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   n-Pr       H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     H     OCF.sub.3                                                                             CF.sub.3 H                                  CH   Et         H     H     OCF.sub.3                                                                             CF.sub.3 H                                  CH   n-Pr       H     H     OCF.sub.3                                                                             CF.sub.3 H                                  CH   Me         H     H     OCHF.sub.2                                                                            CF.sub.3 H                                  CH   Me         H     H     OCF.sub.3                                                                             OCHF.sub.2                                                                              H                                  CH   Me         H     H     CF.sub.3                                                                              OCHF.sub.2                                                                              H                                  CH   Me         F     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     6-F   CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     4-F   CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     2-OMe CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     2-CF.sub.3                                                                           H      CF.sub.3 H                                  CH   Me         H     H     Cl     CF.sub.3 H                                  CH   Et         H     H     CF.sub.3                                                                              OCHF.sub.2                                                                              H                                  CH   Me         H     H     Br     CF.sub.3 H                                  CH   Me         H     H     CN     CF.sub.3 H                                  CH   Et         H     H     CN     CF.sub.3 H                                  CH   Me         H     H     SCF.sub.3                                                                             CF.sub.3 H                                  CH   Me         H     H     H      CF.sub.3 H                                  CH   Me         H     H     CF.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                      H                                  CH   Me         H     H     CF.sub.3                                                                              SCF.sub.3                                                                               H                                  CH   Me         H     H     CF.sub.3                                                                              OMe      H                                  CH   Et         H     H     CF.sub.3                                                                              OEt      H                                  CH   Me         H     H     CF.sub.3                                                                              OCHMe.sub.2                                                                             H                                  CH   Me         H     H     CF.sub.3                                                                              SMe      H                                  CH   Me         H     H     CF.sub.3                                                                              CHF.sub.2                                                                               H                                  CH   Et         H     H     CF.sub.3                                                                              CHF.sub.2                                                                               H                                  CH   Me         H     H     OCF.sub.3                                                                             CHF.sub.2                                                                               H                                  CH   Me         H     H     CF.sub.3                                                                              OCF.sub.2 CHF.sub.2                                                                     H                                  CH   Me         H     H     CF.sub.3                                                                              Cl       H                                  CH   MeCHCH     H     H     CF.sub.3                                                                              CF.sub. 3                                                                               H                                  CH   Me         H     H     CF.sub.3                                                                              CHCHCF.sub.3                                                                            H                                  CH   Me         H     H     CF.sub.3                                                                              OCHF.sub.2                                                                              H                                  CH   Et         H     H     CF.sub.3                                                                              OCHF.sub.2                                                                              H                                  CH   MeOCH.sub.2                                                                               H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Me.sub.2 N H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   MeNH       H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     H     OMe    CF.sub.3 H                                  CH   Me         H     H     CF.sub.3                                                                              SCHF.sub.2                                                                              H                                  CH   Me         H     H     CF.sub.3                                                                              SO.sub.2 CHF.sub.2                                                                      H                                  CH   MeO        H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   MeS        H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     H     CF.sub.3                                                                              CF.sub.3 Me                                 CH   Me         H     H     CF.sub.3                                                                              CF.sub.3 CN                                 CH   Me         H     H     CF.sub.3                                                                              CF.sub.3 OMe                                CH   Me         H     H     CF.sub.3                                                                              CF.sub.3 Cl                                 N    Me         H     H     CF.sub.3                                                                              CF.sub.3 H                                  N    Et         H     H     CF.sub.3                                                                              CF.sub.3 H                                  N    Me         H     H     CF.sub.3                                                                              OCHF.sub.2                                                                              H                                  N    Et         H     H     CF.sub.3                                                                              OCHF.sub.2                                                                              H                                  N    Me         H     H     OCF.sub.3                                                                             CF.sub.3 H                                  N    Me         H     H     OCHF.sub.2                                                                            CF.sub.3 H                                  N    Me         H     H     CN     CF.sub.3 H                                  N    Et         H     H     CN     CF.sub.3 H                                  N    Me         H     H     OCF.sub.3                                                                             OCHF.sub.2                                                                              H                                  N    Me         H     H     CF.sub.3                                                                              OMe      H                                  N    Me         H     H     SCF.sub.3                                                                             CF.sub.3 H                                  ______________________________________                                    

                  TABLE VIII                                                       ______________________________________                                          ##STR27##                                                                     X    R          R.sup.1                                                                              R.sup.2                                                                              R.sup.3                                                                               R.sup.5  R.sup.8                            ______________________________________                                         CH   Me         H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Et         H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   n-Pr       H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     H     OCF.sub.3                                                                             CF.sub.3 H                                  CH   Et         H     H     OCF.sub.3                                                                             CF.sub.3 H                                  CH   n-Pr       H     H     OCF.sub.3                                                                             CF.sub.3 H                                  CH   Me         H     H     OCHF.sub.2                                                                            CF.sub.3 H                                  CH   Me         H     H     OCF.sub.3                                                                             OCHF.sub.2                                                                              H                                  CH   Me         H     H     CF.sub.3                                                                              OCHF.sub.2                                                                              H                                  CH   Me         F     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     6-F   CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     4-F   CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     2-OMe CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     2-CF.sub.3                                                                           H      CF.sub.3 H                                  CH   Me         H     H     Cl     CF.sub.3 H                                  CH   Et         H     H     CF.sub.3                                                                              OCHF.sub.2                                                                              H                                  CH   Me         H     H     Br     CF.sub.3 H                                  CH   Me         H     H     CN     CF.sub.3 H                                  CH   Et         H     H     CN     CF.sub.3 H                                  CH   Me         H     H     SCF.sub.3                                                                             CF.sub.3 H                                  CH   Me         H     H     H      CF.sub.3 H                                  CH   Me         H     H     CF.sub.3                                                                              OCH.sub.2 CF.sub.3                                                                      H                                  CH   Me         H     H     CF.sub.3                                                                              SCF.sub.3                                                                               H                                  CH   Me         H     H     CF.sub.3                                                                              OMe      H                                  CH   Et         H     H     CF.sub.3                                                                              OEt      H                                  CH   Me         H     H     CF.sub.3                                                                              OCHMe.sub.2                                                                             H                                  CH   Me         H     H     CF.sub.3                                                                              SMe      H                                  CH   Me         H     H     CF.sub.3                                                                              CHF.sub.2                                                                               H                                  CH   Et         H     H     CF.sub.3                                                                              CHF.sub.2                                                                               H                                  CH   Me         H     H     OCF.sub.3                                                                             CHF.sub.2                                                                               H                                  CH   Me         H     H     CF.sub.3                                                                              OCF.sub.2 CHF.sub.2                                                                     H                                  CH   Me         H     H     CF.sub.3                                                                              Cl       H                                  CH   MeCHCH     H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     H     CF.sub.3                                                                              CHCHCF.sub.3                                                                            H                                  CH   Me         H     H     CF.sub.3                                                                              OCHF.sub.2                                                                              H                                  CH   Et         H     H     CF.sub.3                                                                              OCHF.sub.2                                                                              H                                  CH   MeOCH.sub.2                                                                               H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Me.sub.2 N H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   MeNH       H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     H     OMe    CF.sub.3 H                                  CH   Me         H     H     CF.sub.3                                                                              SCHF.sub.2                                                                              H                                  CH   Me         H     H     CF.sub.3                                                                              SO.sub.2 CHF.sub.2                                                                      H                                  CH   MeO        H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   MeS        H     H     CF.sub.3                                                                              CF.sub.3 H                                  CH   Me         H     H     CF.sub.3                                                                              CF.sub.3 Me                                 CH   Me         H     H     CF.sub.3                                                                              CF.sub.3 CN                                 CH   Me         H     H     CF.sub.3                                                                              CF.sub.3 OMe                                CH   Me         H     H     CF.sub.3                                                                              CF.sub.3 Cl                                 N    Me         H     H     CF.sub.3                                                                              CF.sub.3 H                                  N    Et         H     H     CF.sub.3                                                                              CF.sub.3 H                                  N    Me         H     H     CF.sub.3                                                                              OCHF.sub.2                                                                              H                                  N    Et         H     H     CF.sub.3                                                                              OCHF.sub.2                                                                              H                                  N    Me         H     H     OCF.sub.3                                                                             CF.sub.3 H                                  N    Me         H     H     OCHF.sub.2                                                                            CF.sub.3 H                                  N    Me         H     H     CN     CF.sub. 3                                                                               H                                  N    Et         H     H     CN     CF.sub.3 H                                  N    Me         H     H     OCF.sub.3                                                                             OCHF.sub.2                                                                              H                                  N    Me         H     H     CF.sub.3                                                                              OMe      H                                  N    Me         H     H     SCF.sub.3                                                                             CF.sub.3 H                                  ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

    ______________________________________                                                     Weight Percent*                                                                Active                                                                         Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74     1-10                                         Oil Suspensions,                                                                              3-50     40-95     0-15                                         Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspension                                                                           10-50     40-84     1-20                                         Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.1-95      5-99.9  0-15                                         High Strength 90-99      0-10     0-2                                          Compositions                                                                   ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals        100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound.Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell,N.J., but other solids, either mined or manufactured, may be used. The moreabsorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed , Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying theactive material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 throughCol. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, Jun. 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., NewYork, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Hand-book", 5th Ed Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

Example A

Wettable Powder

    ______________________________________                                         (difluoromethoxy)-6-methyl-8-[3-(trifluoro-                                                             80%                                                   methyl)phenyl]quinoxaline                                                      sodium alkylnaphthalenesulfonate                                                                         2%                                                   sodium ligninsulfonate    2%                                                   synthetic amorphous silica                                                                               3%                                                   kaolinite                13%                                                   ______________________________________                                    

The ingredients are blended, hamer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

Example B

Wettable Powder

    ______________________________________                                         α-(difluoromethoxy)-6-methyl-8-[3-(trifluoro-                                                     50%                                                   methyl)phenyl]quinoxaline                                                      sodium alkylnaphthalenesulfonate                                                                         2%                                                   low viscosity methyl cellulose                                                                           2%                                                   diatomaceous earth       46%                                                   ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

Example C

Granule

    ______________________________________                                         Wettable Powder of Example B                                                                           5%                                                     attapulgite granules   95%                                                     (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                              ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on the surfaceof attapulgite granules in a double-cone blender. The granules are dried and packaged.

Example D

Extruded Pellet

    ______________________________________                                         α-(difluoromethoxy)-6-methyl-8-[3-(trifluoro-                                                     25%                                                   methyl)phenyl]quinoxaline                                                      anhydrous sodium sulfate 10%                                                   crude calcium ligninsulfonate                                                                            5%                                                   sodium alkylnaphthalenesulfonate                                                                         1%                                                   calcium/magnesium bentonite                                                                             59%                                                   ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42mm openings) may be packaged for use and the fines recycled.

Example E

Low Strength Granule

    ______________________________________                                         α-(difluoromethoxy)-6-methyl-8-[3-(trifluoro-                                                      1%                                                   methyl)phenyl]quinoxaline                                                      N,N-dimethylformamide     9%                                                   attapulgite granules     90%                                                   (U.S.S. 20 to 40 sieve)                                                        ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying ofthe solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

Example F

Granule

    ______________________________________                                         α-(difluoromethoxy)-6-methyl-8-[3-(trifluoro-                                                     80%                                                   methyl)phenyl]quinoxaline                                                      wetting agent             1%                                                   crude ligninsulfonate salt (containing                                                                  10%                                                   5-20% of the natural sugars)                                                   attapulgite clay          9%                                                   ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the lair flow is adjusted to gently fluidize the material, and a fine-spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until thewater content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally14-100 mesh (1410-149 microns), and packaged for use.

Example G

Aqueous Suspension

    ______________________________________                                         α-(difluoromethoxy)-6-methyl-8-[3-(trifluoro-                                                      40%                                                  methyl)phenyl]quinoxaline                                                      polyacrylic acid thickener                                                                              0.3%                                                  dodecylphenol polyethylene glycol ether                                                                 0.5%                                                  disodium phosphate         1%                                                  monosodium phosphate     0.5%                                                  polyvinyl alcohol        1.0%                                                  water                    56.7%                                                 ______________________________________                                    

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

Example H

High Strength Concentrate

    ______________________________________                                         α-(difluoromethoxy)-6-methyl-8-[3-(trifluoro-                                                      99%                                                  methyl)phenyl]quinoxaline                                                      silica aerogel           0.5%                                                  synthetic amorphous silica                                                                              0.5%                                                  ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

Example I

Wettable Powder.

    ______________________________________                                         α-(difluoromethoxy)-6-methyl-8-[3-(trifluoro-                                                      90%                                                  methyl)phenyl]quinoxaline                                                      dioctyl sodium sulfosuccinate                                                                           0.1%                                                  synthetic fine silica    9.9%                                                  ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.

Example J

Wettable Powder

    ______________________________________                                         α-(difluoromethoxy)-6-methyl-8-[3-(trifluoro-                                                     40%                                                   methyl)phenyl]quinoxaline                                                      sodium ligninsulfonate   20%                                                   montmorillonite clay     40%                                                   ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

Example K

Oil Suspension

    ______________________________________                                         α-(difluoromethoxy)-6-methyl-8-[3-(trifluoro-                                                     35%                                                   methyl)phenyl]quinoxaline                                                      blend of polyalcohol carboxylic                                                                          6%                                                   esters and oil soluble petroleum                                               sulfonates                                                                     xylene                   59%                                                   ______________________________________                                    

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

Example L

Dust

    ______________________________________                                         α-(difluoromethoxy)-6-methyl-8-[3-(trifluoro-                                                     10%                                                   methyl)phenyl]quinoxaline                                                      attapulgite              10%                                                   Pyrophyllite             80%                                                   ______________________________________                                    

The active ingredient is blended with attapulgite and then passed through ahammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.

Example M

Oil Suspension

    ______________________________________                                         α-(difluoromethoxy)-6-methyl-8-[3-(trifluoro-                                                     25%                                                   methyl)phenyl]quinoxaline                                                      polyoxyethylene sorbitol hexaoleate                                                                      5%                                                   highly aliphatic hydrocarbon oil                                                                        70%                                                   ______________________________________                                    

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

UTILITY

Test results indicate compounds of this invention are active postemergence and preemergence herbicides. Many compounds in this invention are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops such as barley (Hordeum yulgare), corn (Zea mays), cotton (Gossypium hirsutum), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), wheat (Triticum aestiyum), and to vegetable corps. Grass and broadleaf weed species controlled include, but are not limited to, barnyardgrass (Echinochloa crusgalli), bedstraw (Galium aparine ), blackgrass (Alopecurus myosuroides), cheatgrass (Bromussecalinus), chickweed (Stellaria media), crabgrass (Digitaria spp.), foxtail (setaria spp.), lambsquarters (Chenopodium spp.), velvetleaf (Afutilon theophrasti), wild buckwheat (Polygonum convolvulus) and wild oats (Avena fatua).

These compounds also have utility for weed control of selected vegetation in specified areas such as around storage tanks, parking lots, highways, and railways; in fallow crop areas; and in citrus and plantation crops such as banana, coffee, oil palm, and rubber. Alternatively, these compounds are useful to modify plant growth.

Rates of application for compounds of this invention are determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general terms, the subject compounds should be applied at rates from 0.01 to 20 kg/ha with a preferred rate range of 0.02 to 2 kg/ha. Although a small number of compounds show slight herbicidal activity at the rates tested, it is anticipated these compounds are herbicidally active at higher application rates. One skilled in the art can easily determine application rates necessary for desired level of weed control.

Compounds of this invention may be used alone or in combination with other commercial herbicides, insecticides, or fungicides. The following list exemplifies some of the herbicides suitable for use in mixtures. A combination of a compound from-this invention with one or more of the following herbicides may be particularly useful for weed control.

    ______________________________________                                         Common Name Chemical Name                                                      ______________________________________                                         acetochlor  2-chloro-N-(ethoxymethyl)-N-(2-ethyl-                                          6-methylphenyl)acetamide                                           acifluorfen 5-[2-chloro-4-(trifluoromethyl)-                                               phenoxy]-2-nitrobenzoic acid                                       aclonifen   2-chloro-6-nitro-3-phenoxybenzenamine                              acrolein    2-propenal                                                         alachlor    2-chloro-N-(2,6-diethylphenyl)-N-                                              (methoxymethyl)acetamide                                           alloxydim   methyl 2,2-dimethyl-4,6-dioxo-5-[1-                                            [(2-propenyloxy)amino]butylidene]-                                             cyclohexanecarboxylate                                             ametryn     N-ethyl-N'-(1-methylethyl)-6-(methyl-                                          thio)-1,3,5-triazine-2,4-diamine                                   amitrole    1H-1,2,4-triazol-3-amine                                           AMS         ammonium sulfamate                                                 anilofos    S-[2-[(4-chlorophenyl)(1-methyl-                                               ethyl)amino]-2-oxoethyl]O,O-                                                   dimethylphosphorodithioate                                         asulam      methyl [(4-aminophenyl)sulfonyl]-                                              carbamate                                                          atrazine    6-chloro-N-ethyl-N'-(1-methylethyl)-                                           1,3,5-triazine-2,4-diamine                                         aziprotryne 4-azido-N-(1-methylethyl)-6-methyl-                                            thio-1,3,5-triazin-2-amine                                         azoluron    N-(1-ethyl-1H-pyrazol-5-yl)-N'-                                                phenylurea                                                         barban      4-chloro-2-butynyl 3-chlorocarbamate                               benazolin   4-chloro-2-oxo-3(2H)-benzothiazole                                             acetic acid                                                        benfluralin N-butyl-N-ethyl-2,6-dinitro-4-                                                 (trifluoromethyl)benzenamine                                       bensulfuron 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)-                                          amino]methylcarbonyl]amino]-                                                   sulfonyl]methyl]benzoic acid,                                                  methyl ester                                                       bensulide   O,O-bis(1-methylethyl) S-[2-[(phenyl-                                          sulfonyl)amino]ethyl]phosphoro-                                                dithioate                                                          bentazon    3-(1-methylethyl)-(1H)-2,1,3-benzo-                                            thiadiazin-4(3H)-one, 2,2-dioxide                                  benzofluor  N-[4-(ethylthio)-2-(trifluoromethyl)-                                          phenyl]methanesulfonamide                                          benzoylprop N-benzoyl-N-(3,4-dichlorophenyl)-DL-                                           alanine                                                            benzthiazuron                                                                              N-2-benzothiazolyl-N'-methylurea                                   bialaphos   4-(hydroxymethylphosphinyl)-L-2-                                               aminobutanoyl-L-alanyl-L-alanine                                   bifenox     methyl 5-(2,4-dichlorophenoxy)-2-                                              nitrobenzoate                                                      bromacil    5-bromo-6-methyl-3-(1-methylpropyl)-                                           2,4(1H,3H)pyrimidinedione                                          *bromobutide                                                                               (+)2-bromo-3,3-dimethyl-N-(1-methyl-                                           1-phenylethyl)butanamide                                           bromofenoxim                                                                               3,5-dibromo-4-hydroxybenzaldhyde                                               O-(2,4-dinitrophenyl)oxime                                         bromoxynil  3,5-dibromo-4-hydroxybenzonitrile                                  bromuron    N'-(4-bromophenyl)-N,N-dimethylurea                                buminafos   dibutyl [1-(butylamino)cyclohexyl]-                                            phosphonate                                                        butachlor   N-(butoxymethyl)-2-chloro-N-(2,6-                                              diethylphenyl)acetamide                                            butamifos   O-ethyl O-(5-methyl-2-nitrophenyl)(1-                                          methylpropyl)phosphoramidothioate                                  buthidazole 3-[5-(1,1-dimethylethyl)-1,3,4-                                                thiadiazol-2-yl]-4-hydroxy-1-                                                  methyl-2-imidazolidinone                                           butralin    4-(1,1-dimethylethyl)-N-(1-methyl-                                             propyl)-2,6-dinitrobenzenamine                                     butylate    S-ethyl bis(2-methylpropyl)-                                                   carbamothioate                                                     cacodylic acid                                                                             dimethyl arsinic oxide                                             carbetamide (R)-N-ethyl-2-[[(phenylamino)-                                                 carbonyl]oxy]propanamide                                           CDAA        2-chloro-N,N-di-2-propenylacetamide                                CDEC        2-chloroallyl diethyldithiocarbamate                               chlomethoxyfen                                                                             4-(2,4-dichlorophenoxy)-2-methoxy-1-                                           nitrobenzene                                                       chloramben  3-amino-2,5-dichlorobenzoic acid                                   chlorbromuron                                                                              3-(4-bromo-3-chlorophenyl)-1-methoxy-                                          1-methylurea                                                       chlorbufam  1-methyl-2-propynl(3-chlorophenyl)-                                            carbamate                                                          chlorfenac  2,3,6-trichlorobenzeneacetic acid                                  chlorflurecol-                                                                             methyl 2-chloro-9-hydroxy-9H-                                      methyl      fluorene-9-carboxylate                                             chloridazon 5-amino-4-chloro-2-phenyl-3(2H)-                                               pyridazinone                                                       chlorimuron 2-[[[[(4-chloro-6-methoxy-2-                                                   pyrimidinyl)ethylamino]carbonyl]-                                              amino]sulfonyl]benzoic acid, ethyl                                             ester                                                              chlornitrofen                                                                              1,3,5-trichloro-2-(4-nitrophenoxy)-                                            benzene                                                            chloropicrin                                                                               trichloronitromethane                                              chloroxuron N'-[4-(4-chlorophenoxy)phenyl]-N,N-                                            dimethylurea                                                       chlorpropham                                                                               1-methylethyl 3-chlorophenylcarbamate                              chlorsulfuron                                                                              2-chloro-N-[[(4-methoxy-6-methyl-                                              1,3,5-triazin-2-yl)-amino]-                                                    carbonyl]benzenesulfonamide                                        chlorthal-  dimethyl 2,3,5,6-tetrachloro-1,4-                                  dimethyl    benzenedicarboxylate                                               chlorthiamid                                                                               2,6-dichlorobenzene carbothioamide                                 chlortoluron                                                                               N'-(3-chloro-4-methylphenyl)-N,N-                                              dimethylurea                                                       cinmethylin exo-1-methyl-4-(1-methylethyl)-2-[(2-                                          methylphenyl)methoxy]-7-oxabicyclo-                                            [2.2.1]heptane                                                     clethodim   (E,E)-(+)-2-[1-[[(3-chloro-2-                                                  propenyl)oxy]imino]propyl]-5-[2-                                               (ethylthio)propyl]-3-hydroxy-2-                                                cyclohexen-1-one                                                   clomazone   2-[(2-chlorophenyl)methyl]-4,4-                                                dimethyl-3-isoxazolidinone                                         cloproxydim (E,E)-2-[1-[[(3-chloro-2-propenyl)-                                            oxy)imino]butyl]-5-[2-(ethylthio)-                                             propyl]-3-hydroxy-2-cyclohexen-1-                                              one                                                                clopyralid  3,6-dichloro-2-pyridinecarboxylic                                              acid                                                               CMA         calcium salt of MAA                                                cyanazine   2-[[4-chloro-6-(ethylamino)-1,3,5-                                             triazin-2-yl]amino]-2-methyl-                                                  propanenitrile                                                     cycloate    S-ethyl cyclohexylethylcarbamothioate                              cycloxydim  2-[1-ethoxyimino)butyl]-3-hydroxy-5-                                           (tetrahydro-2H-thiopyran-3-yl)-2-                                              cyclohexene-1-one                                                  cycluron    3-cyclooctyl-1,1-dimethylurea                                      cyperquat   1-methyl-4-phenylpyridinium                                        cyprazine   2-chloro-4-(cyclopropylamino)-6-                                               (isopropylamino)-s-triazine                                        cyprazole   N-[5-(2-chloro-1,1-dimethylethyl)-                                             1,3,4-thiadiazol-2-yl]cyclopropane-                                            carboxamide                                                        cypromid    3',4'-dichlorocyclopropane-                                                    carboxanilide                                                      dalapon     2,2-dichloropropanoic acid                                         dazomet     tetrahydro-3,5-dimethyl-2H-1,3,5-                                              thiadiazine-2-thione                                               DCPA        dimethyl 2,3,5,6-tetrachloro-1,4-                                              benzenedicarboxylate                                               desmedipham ethyl [3-[[(phenylamino)carbonyl]-                                             oxy]phenyl]carbamate                                               desmetryn   2-(isopropylamino)-4-(methylamino)-6-                                          (methylthio)-s-triazine                                            diallate    S-(2,3-dichloro-2-propenyl)bis(1-                                              methylethyl)carbamothioate                                         dicamba     3,6-dichloro-2-methoxybenzoic acid                                 dichlobenil 2,6-dichlorobenzonitrile                                           dichlorprop (+)-2-(2,4-dichlorophenoxy)propanoic                                           acid                                                               *diclofopmethyl                                                                            (+)-2-[4-(2,4-dichlorophenoxy)-                                                phenoxy]propanoic acid, methyl                                                 ester                                                              diethatyl   N-(chloroacetyl)-N-(2,6-diethyl-                                               phenyl)glycine                                                     difenoxuron N'-[4-(4-methoxyphenoxy)phenyl]-N,N-                                           dimethylurea                                                       difenzoquat 1,2-dimethyl-3,5-diphenyl-1H-                                                  pyrazolium ion                                                     diflufenican                                                                               N-(2,4-difluorophenyl)-2-(3-                                                   trifluoromethylphenoxy)pyridine-3-                                             carboxamide                                                        dimefuron   N'-[3-chloro-4-[5-(1,1-dimethyl-                                               ethyl)-2-oxo-1,3,4-oxadiazol-3(2H)-                                            yl]phenyl]-N,N-dimethylurea                                        dimethachlor                                                                               2-chloro-N-(2,6-dimethylphenyl)-N-(2-                                          methoxyethyl)acetamide                                             dimethametryn                                                                              N-(1,2-dimethylpropyl)-N'-ethyl-6-                                             (methylthio)-1,3,5-triazine-2,4-                                               diamine                                                            dimethipin  2,3-dihydro-5,6-dimethyl-1,4-dithiin                                           1,1,4,4-tetraoxide                                                 dimethylarsinic                                                                            dimethylarsinic acid                                               dinitramine N.sup.3,N.sup.3 -diethyl-2,4-dinitro-6-(tri-                                   fluoromethyl)-1,3-benzenediamine                                   dinoseb     2-(1-methylpropyl)-4,6-dinitrophenol                               dinoterb    2-(1,1-dimethylethyl)-4,6-dinitro-                                             phenol                                                             diphenamid  N,N-dimethyl-α-phenylbenzeneacetamide                        dipropetryn 6-(ethylthio)-N,N'-bis(1-methyl-                                               ethyl)-1,3,5-triazine-2,4-diamine                                  diquat      6,7-dihydrodipyrido[1,2-a:2',-1'-c]-                                           pyrazinediium ion                                                  diuron      N'-(3,4-dichlorophenyl)-N,N-                                                   dimethylurea                                                       DNOC        2-methyl-4,6-dinitrophenol                                         DPX-V9360   2-[[(4,6-dimethoxypyrimidin-2-yl)-                                             aminocarbonyl]aminosulfonyl]-N,N-                                              dimethyl-3-pyridinecarboxamide                                     DSMA        disodium salt of MAA                                               dymron      N-(4-methylphenyl)-N'-(1-methyl-1-                                             phenylethyl)urea                                                   eglinazine-ethyl                                                                           N-[4-chloro-6-(ethylamino)-1,3,5-                                              triazin-2-yl]glycine ethyl ester                                   endothall   7-oxabicyclo[2.2.1]heptane-2,3-                                                dicarboxylic acid                                                  EPTC        S-ethyl dipropylcarbamothioate                                     ethalfluralin                                                                              N-ethyl-N-(2-methyl-2-propenyl)-2,6-                                           dinitro-4-(trifluoromethyl)                                                    benzenamine                                                        ethidimuron N-[5-(ethylsulfonyl)-1,3,4-thia-                                               diazol-2-yl]-N,N'-dimethylurea                                     *ethofumesate                                                                              (+)-2-ethoxy-2,3-dihydro-3,3-                                                  dimethyl-5-benzofuranyl methane-                                               sulfonate                                                          fenac       2,3,6-trichlorobenzeneacetic acid                                  *fenoprop   (+)-2-(2,4,5-trichlorophenoxy)-                                                propanoic acid                                                     *fenoxaprop (+)-2-[4-[(6-chloro-2-benzoxazolyl)-                                           oxy]phenoxy]propanoic acid                                         fenuron     N,N-dimethyl-N'-phenylurea                                         fenuron TCA Salt of fenuron and TCA                                            flamprop-M- 1-methylethyl N-benzoyl-N-(3-chloro-                               isopropyl   4-fluorophenyl)-D-alanine                                          flamprop-methyl                                                                            methyl N-benzoyl-N-(3-chloro-4-                                                fluorophenyl)-DL-alaninate                                         *fluazifop  (+)-2-[4-[[5-(trifluoromethyl)-2-                                              pyridinyl]oxy]phenoxy]propanoic                                                acid                                                               fluazifop-P (R)-2-[4-[[5-(trifluoromethyl)-2-                                              pyridinyl]oxy]phenoxy]propanoic                                                acid                                                               fluchloralin                                                                               N-(2-chloroethyl)-2,6-dinitro-N-                                               propyl-4-(trifluoromethyl)-                                                    benzenamine                                                        fluometuron N,N-dimethyl-N'-[3-(trifluoro-                                                 methyl)phenyl]urea                                                 fluralin    N-butyl-N-ethyl-2,6-dinitro-4-                                                 (trifluoromethyl)benzenamine                                       fluorodifen p-nitrophenyl α,α,α-trifluoro-2-                             nitro-p-tolyl ether                                                fluoroglycofen                                                                             carboxymethyl 5-[2-chloro-4-(tri-                                              fluoromethyl)phenoxy]-2-nitro-                                                 benzoate                                                           flurecol-butyl                                                                             butyl 9-hydroxy-9H-fluorene-9-                                                 carboxylate                                                        fluridone   1-methyl-3-phenyl-5-[3-(trifluoro-                                             methyl)phenyl]-4(1H)-pyridinone                                    flurochloridone                                                                            3-chloro-4-(chloromethyl)-1-[3-                                                (trifluoromethyl)phenyl]-2-                                                    pyrrolidinone                                                      fluroxypyr  [(4-amino-3,5-dichloro-6-fluoro-2-                                             pyridinyl)oxy]acetic acid                                          fomesafen   5-[2-chloro-4-(trifluoromethyl)-                                               phenoxy]-N-(methylsulfonyl)-2-                                                 nitrobenzamide                                                     fosamine-   ethyl hydrogen (aminocarbonyl)-                                    ammonium    phosphonate ammonium ethyl                                         glufosinate-                                                                               ammonium 2-amino-4-(hydroxymethyl-                                 ammonium    phosphinyl)butanoate                                               glyphosate  N-(phosphonomethyl)glycine                                         haloxyfop   2-[4-[[3-chloro-5-(trifluoromethyl)-                                           2-pyridinyl]oxy]-phenoxy]propanoic                                             acid                                                               hexaflurate potassium hexafluoroarsenate                                       hexazinone  3-cyclohexyl-6-(dimethylamino)-1-                                              methyl-1,3,5-triazine-2,4-                                                     (1H,3H)dione                                                       imazamethabenz                                                                             6-(4-isopropyl-4-methyl-5-oxo-2-                                               imidazolin-2-yl)-m-toluic acid,                                                methyl ester and 6-(4-isopropyl-4-                                             methyl-5-oxo-2-imidazolin-2-yl)-p-                                             toluic acid, methyl ester                                          imazapyr    (+)-2-[4,5-dihydro-4-methyl-4-(1-                                              methylethyl)-5-oxo-1H-imidazol-2-                                              yl]-3-pyridinecarboxylic acid                                      imazaquin   2-[4,5-dihydro-4-methyl-4-(1-methyl-                                           ethyl)-5-oxo-1H-imidazol-2-yl]-3-                                              quinolinecarboxylic acid                                           imazethapyr (+)-2-[4,5-dihydro-4-methyl-4-(1-                                              methylethyl)-5-oxo-1H-imidazol-2-                                              yl]-5-ethyl-3-pyridine carboxylic                                              acid                                                               ioxynil     4-hydroxy-3,5-diiodobenzonitrile                                   isocarbamid N-(2-methylpropyl)-2-oxo-1-                                                    imidazolidinecarboxamide                                           isopropalin 4-(1-methylethyl)-2,6-dinitro-N,N-                                             dipropylbenzenamine                                                isoproturon N-(4-isopropylphenyl)-N',N'-                                                   dimethylurea                                                       isouron     N'-[5-(1,1-dimethylethyl)-3-                                                   isoxazolyl]-N,N-dimethylurea                                       isoxaben    N-[3-(1-ethyl-1-methylpropyl)-5-                                               isoxazolyl]-2,6-dimethoxybenzamide                                 karbutilate 3-[[(dimethylamino)carbonyl]-                                                  amino]phenyl-(1,1-dimethylethyl)-                                              carbamate                                                          lactofen    (+)-2-ethoxy-1-methyl-2-oxoethyl-5-                                            [2-chloro-4-(trifluoromethyl)-                                                 phenoxy]-2-nitrobenzoate                                           lenacil     3-cyclohexyl-6,7-dihydro-1H-cyclo-                                             pentapyrimidine-2,4(3H,5H)-dione                                   linuron     N'-(3,4-dichlorophenyl)-N-methoxy-N-                                           methylurea                                                         MAA         methylarsonic acid                                                 MAMA        monoammonium salt of MAA                                           MCPA        (4-chloro-2-methylphenoxy)acetic acid                              MCPA-thioethyl                                                                             S-ethyl (4-chloro-2-methylphenoxy)-                                            ethanethioate                                                      MCPB        4-(4-chloro-2-methylphenoxy)butanoic                                           acid                                                               mecoprop    (+)-2-(4-chloro-2-methylphenoxy)-                                              propanoic acid                                                     mefenacet   2-(2-benzothiazolyloxy)-N-methyl-N-                                            phenyl acetamide                                                   mefluidide  N-[2,4-dimethyl-5-[[(trifluoro-                                                methyl)sulfonyl]amino]phenyl]-                                                 acetamide                                                          metamitron  4-amino-3-methyl-6-phenyl-1,2,4-                                               triazin-5(4H)-one                                                  metazachlor 2-chloro-N-(2,6-dimethylphenyl)-N-                                             (1(H)-pyrazol-1-ylmethyl)acetamide                                 methabenz-  1,3-dimethyl-3-(2-benzothiazolyl)urea                              thiazuron                                                                      methalpropalin                                                                             N-(2-methyl-2-propenyl)-2,6-dinitro-                                           N-propyl-4-(trifluoromethyl)-                                                  benzenamide                                                        metham      methylcarbamodithioic acid                                         methazole   2-(3,4-dichlorophenyl)-4-methyl-                                               1,2,4-oxadiazolidine-3,5-dione                                     methoxuron  N'-(3-chloro-4-methoxyphenyl)-N,N-                                             dimethylurea                                                       methoxyphenone                                                                             (4-methoxy-3-methylphenyl)(3-                                                  methylphenyl)methanone                                             methyldymron                                                                               N-methyl-N'-(1-methyl-1-phenyl-                                                ethyl)-N-phenylurea                                                metobromuron                                                                               N'-(4-bromophenyl)-N-methoxy-N-                                                methylurea                                                         metolachlor 2-chloro-N-(2-ethyl-6-methylphenyl)-                                           N-(2-methoxy-1-methylethyl)-                                                   acetamide                                                          metoxuron   N'-(3-chloro-4-methoxyphenyl)-N,N-                                             dimethylurea                                                       metribuzin  4-amino-6-(1,1-dimethylethyl)-3-                                               (methylthio)-1,2,4-triazin-5(4H)-                                              one                                                                metsulfuron 2-[[[[(4-methoxy-6-methyl-1,3,5-                                   methyl      triazin-2-yl)amino]carbonyl]amino]-                                            sulfonyl]benzoic acid, methyl ester                                MH          1,2-dihydro-3,6-pyridazinedione                                    molinate    S-ethyl hexahydro-1H-azepine-1-carbo-                                          thioate                                                            monalide    N-(4-chlorophenyl)-2,2-dimethyl-                                               pentanamide                                                        monolinuron 3-(p-chlorophenyl)-1-methoxy-1-                                                methyl-urea                                                        monuron     N'-(4-chlorophenyl)-N,N-dimethylurea                               MSMA        monosodium salt of MAA                                             naproanilide                                                                               2-(2-naphthalenyloxy)-N-phenyl-                                                propanamide                                                        napropamide N,N-diethyl-2-(1-naphthalenyloxy)-                                             propanamide                                                        naptalam    2-[(1-naphthalenylamino)carbonyl]-                                             benzoic acid                                                       neburon     1-butyl-3-(3,4-dichlorophenyl)-1-                                              methylurea                                                         nitralin    4-methylsulfonyl-2,6-dinitro-N,N-                                              dipropylaniline                                                    nitrofen    2,4-dichloro-1-(4-nitrophenoxy)-                                               benzene                                                            nitrofluorfen                                                                              2-chloro-1-(4-nitrophenoxy)-4-(tri-                                            fluoromethyl)benzene                                               norea       N,N-dimethyl-N'-(octahydro-4,7-                                                methano-1H-inden-5-yl)urea-                                                    3aα,4α,5α,7α,7aα-isomer              norflurazon 4-chloro-5-(methylamino)-2-[3-                                                 (trifluoromethyl)phenyl]-3(2H)-                                                pyridazinone                                                       orbencarb   S-[2-(chlorophenyl)methyl]diethyl-                                             carbamothioate                                                     oryzalin    4-(dipropylamino)-3,5-dinitrobenzene-                                          sulfonamide                                                        oxadiazon   3-[2,4-dichloro-5-(1-methylethoxy)-                                            phenyl]-5-(1,1-dimethylethyl)-                                                 1,3,4-oxadiazol-2(3H)-one                                          oxyfluorfen 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-                                        (trifluoromethyl)benzene                                           paraquat    1,1'-dimethyl-4,4'-dipyridinium ion                                pebulate    S-propyl butylethylcarbamothioate                                  pendimethalin                                                                              N-(1-ethylpropyl)-3,4-dimethyl-2,6-                                            dinitrobenzenamine                                                 perfluidone 1,1,1-trifluoro-N-[2-methyl-4-                                                 (phenylsulfonyl)phenyl]methane-                                                sulfonamide                                                        phenisopham 3-[[(1-methylethoxy)carbonyl]-                                                 amino]phenyl ethylphenylcarbamate                                  phenmedipham                                                                               3-[(methoxycarbonyl)amino]phenyl(3-                                            methylphenyl)carbamate                                             picloram    4-amino-3,5,6-trichloro-2-pyridine-                                            carboxylic acid                                                    piperophos  S-[2-(2-methyl-1-piperidinyl)-2-oxo-                                           ethyl]O,O-dipropyl phosphoro-                                                  dithioate                                                          pretilachlor                                                                               2-chloro-N-(2,6-diethylphenyl)-N-(2-                                           propoxyethyl)acetamide                                             procyazine  2-[[4-chloro-6-(cyclopropylamino)-                                             1,3,5-triazine-2-yl]amino]-2-                                                  methylpropanenitrile                                               prodiamine  2,4-dinitro-N3,N3-dipropyl-6-(tri-                                             fluoromethyl)-1,3-benzenediamine                                   profluralin N-(cyclopropylmethyl)-2,6-dinitro-N-                                           propyl-4-(trifluoromethyl)-                                                    benzenamine                                                        proglinazine-                                                                              N-[4-chloro-6-[(1-methylethyl)amino]-                              ethyl       1,3,5-triazin-2-yl]-glycine ethyl                                              ester                                                              prometon    6-methoxy-N,N'-bis(1-methylethyl)-                                             1,3,5-triazine-2,4-diamine                                         prometryn   N,N'-bis(1-methylethyl)-6-(methyl-                                             thio)-1,3,5-triazine-2,4-diamine                                   pronamide   3,5-dichloro-N-(1,1-dimethyl-2-                                                propynyl)benzamide                                                 propachlor  2-chloro-N-(1-methylethyl)-N-phenyl-                                           acetamide                                                          propanil    N-(3,4-dichlorophenyl)propanamide                                  propaquizafop                                                                              2-[[(1-methylethylidene)amino]oxy]-                                            ethyl-2-[4-[(6-chloro-2-                                                       quinoxalinyl)oxy]phenoxy]-                                                     propanoate                                                         propazine   6-chloro-N,N'-bis(1-methylethyl)-                                              1,3,5-triazine-2,4-diamine                                         propham     1-methylethyl phenylcarbamate                                      propyzamide 3,5-dichloro-N-(1,1-dimethyl-2-                                                propynl)benzamide                                                  prosulfalin N-[[4-(dipropylamino)-3,5-dinitro-                                             phenyl]sulfonyl]-S,S-dimethyl-                                                 sulfilimine                                                        prosulfocarb                                                                               S-benzyldipropylthiocarbamate                                      prynachlor  2-chloro-N-(1-methyl-2-propynyl)-                                              acetanilide                                                        pyrazon     5-amino-4-chloro-2-phenyl-3(2H)-                                               pyridazinone                                                       pyrazosulfuron-                                                                            ethyl 5-[[[[(4,6-dimethoxy-2-                                      ethyl       pyrimidinyl)amino]carbonyl]-                                                   amino]sulfonyl]-1-methyl-1H-                                                   pyrazole-4-carboxylate                                             pyrazoxyfen 2-[[4-(2,4-dichlorobenzoyl)-1,3-                                               dimethyl-1H-pyrazol-5-yl]oxy]-1-                                               phenylethanone                                                     pyridate    O-(6-chloro-3-phenyl-4-pyridazinyl)                                            S-octyl carbonothioate                                             quizalofop ethyl                                                                           (+)-2-[4-[(6-chloro-2-quinoxalinyl)-                                           oxy]phenoxy]propanoic acid, ester                                  secbumeton  N-ethyl-6-methoxy-N'-(1-methyl-                                                propyl)-1,3,5-triazine-2,4-diamine                                 sethoxydim  2-[1-(ethoxyimino)butyl]-5-[2-(ethyl-                                          thio)propyl]-3-hydroxy-2-cyclo-                                                hexen-1-one                                                        siduron     N-(2-methylcyclohexyl)-N'-phenylurea                               simazine    6-chloro-N,N'-diethyl-1,3,5-triazine-                                          2,4-diamine                                                        simetryn    N,N'-diethyl-6-(methylthio)-1,3,5-                                             triazine-2,4-diamine                                               sodium chlorate                                                                            sodium chlorate                                                    sodium mono-                                                                               chloroacetic acid, sodium salt                                     chloroacetate                                                                  sulfometuron                                                                               2-[[[[(4,6-dimethyl-2-pyrimidinyl)-                                methyl      amino]carbonyl]amino]sulfonyl]-                                                benzoic acid, methyl ester                                         2,4,5-T     (2,4,5-trichlorophenoxy)acetic acid                                2,3,6-TBA   2,3,6-trichlorobenzoic acid                                        TCA         trichloroacetic acid                                               tebutam     2,2-dimethyl-N-(1-methylethyl)-N-                                              (phenylmethyl)propanamide                                          tebuthiuron N-[5-(1,1-dimethylethyl)-1,3,4-                                                thiadiazol-2-yl]-N,N'-dimethylurea                                 terbacil    5-chloro-3-(1,1-dimethylethyl)-6-                                              methyl-2,4(1H,3H)-pyrimidinedione                                  terbuchlor  N-(butoxymethyl)-2-chloro-N-[2-(1,1-                                           dimethylethyl)-6-methylphenyl]-                                                acetamide                                                          terbumeton  N-(1,1-dimethylethyl)-N'-ethyl-6-                                              methoxy-1,3,5-triazine-2,4-diamine                                 terbuthylazine                                                                             2-(tert-butylamino)-4-chloro-6-                                                (ethylamino)-s-triazine                                            terbutol    2,6-di-tert-butyl-p-tolyl methyl-                                              carbamate                                                          terbutryn   N-(1,1-dimethylethyl)-N'-ethyl-6-                                              (methylthio)-1,3,5-triazine-2,4-                                               diamine                                                            thifensulfuron                                                                             3-[[[[(4-methoxy-6-methyl-1,3,5-                                               triazin-2-yl)amino]carbonyl]amino]-                                            sulfonyl]-2-thiophenecarboxylic                                                acid, methyl ester                                                 thiameturonmethyl                                                                          methyl 3-[[[[(4-methoxy-6-methyl-                                              1,3,5-triazin-2-yl)amino]carbonyl]-                                            amino]sulfonyl]2-thiophene-                                                    carboxylate                                                        thiazafluron                                                                               N,N'-dimethyl-N-[5-(trifluoromethyl)-                                          1,3,4-thiadiazol-2-yl]urea                                         thiobencarb S-[(4-chlorophenyl)methyl]diethyl-                                             carbamothioate                                                     tiocarbazil S-(phenylmethyl) bis(1-methylpropyl)-                                          carbamothioate                                                     tralkoxydim 2-[1-(ethoxyimino)propyl]-3-hydroxy-                                           5-(2,4,6-trimethylphenyl)-2-                                                   cyclohexen-1-one                                                   triallate   S-(2,3,3-trichloro-2-propenyl)bis(1-                                           methylethyl)carbamothioate                                         triasulfuron                                                                               2-(2-chloroethoxy)-N-[[(4-methoxy-6-                                           methyl-1,3,5-triazin-2-yl)amino]-                                              carbonyl]benzenesulfonamide                                        tribenuron methyl                                                                          2-[[[[N-(4-methoxy-6-methyl-1,3,5-                                             triazine-2-yl)-N-methylamino]-                                                 carbonyl]amino]sulfonyl]benzoic                                                acid, methyl ester                                                 triclopyr   [(3,5,6-trichloro-2-pyridinyl)oxy]-                                            acetic acid                                                        *tridiphane (+)2-(3,5-dichlorophenyl)-2-(2,2,2-                                            trichloroethyl)oxirane                                             trietazine  6-chloro-N,N,N'-triethyl-1,3,5-                                                triazine-2,4-diamine                                               trifluralin 2,6-dinitro-N,N-dipropyl-4-                                                    (trifluoromethyl)benzenamine                                       trimeturon  1-(p-chlorophenyl)-2,3,3-trimethyl-                                            pseudourea                                                         2,4-D       (2,4-dichlorophenoxy)acetic acid                                   2,4-DB      4-(2,4-dichlorophenoxy)butanoic acid                               vernolate   S-propyl dipropylcarbamothioate                                    xylachlor   2-chloro-N-(2,3-dimethylphenyl)-N-(1-                                          methylethyl)acetamide                                              ______________________________________                                    

Selective herbicidal properties of the subject compounds were discovered ingreenhouse tests as described below.

    __________________________________________________________________________     TABLE OF COMPOUNDS                                                              ##STR28##                                                                     CMPD                                                                               R  R.sup.1                                                                           R.sup.3                                                                             Y  Z       Q       n m.p. (°C.)                          __________________________________________________________________________     1   Me H  CF.sub.3                                                                            CH CH      COCH.sub.2 CF.sub.3                                                                    0 oil                                        2   Me H  CF.sub.3                                                                            N  COCH.sub.2 CF.sub.3                                                                    CH      0 114-117                                    3   Me H  CF.sub.3                                                                            N  COMe    CH      0 141-142                                    4   Me H  CF.sub.3                                                                            N  CH      COMe    0 119-121                                    5   Me H  CF.sub.3                                                                            N  N       COCH.sub.2 CF.sub.3                                                                    1 168-169                                    6   Me H  CF.sub.3                                                                            N  N       COCH.sub.2 CF.sub.3                                                                    0 140-141                                    7   Me H  CF.sub.3                                                                            N  CH      COCH.sub.2 CF.sub.3                                                                    0 46-48                                      8   Me H  CF.sub.3                                                                            N  CCF.sub.3                                                                              CH      0 93-94                                      9   Me H  CF.sub.3                                                                            N  CH      CCF.sub.3                                                                              0 117-118                                    10  Me H  CF.sub.3                                                                            N  N       COCHF.sub.2                                                                            1 128-129                                    11  Me H  CF.sub.3                                                                            N  N       COCHF.sub.2                                                                            0 109-110                                    12  Me H  CF.sub.3                                                                            N  N       COMe    1 147-148                                    13  Me H  CF.sub.3                                                                            N  N       COMe    0 117-118                                    14  Me H  CF.sub.3                                                                            N  COCHF.sub.2                                                                            CH      0 105-106                                    15  Me H  CF.sub.3                                                                            N  CH      COCHF.sub.2                                                                            0 103-104                                    16  Me H  CN   N  CCF.sub.3                                                                              CH      0 165-166                                    17  Me H  CN   N  CH      CCF.sub.3                                                                              0 171-172                                    18  Me H  CF.sub.3                                                                            CH CH      COCHF.sub.2                                                                            0 74-75                                      19  Et H  CF.sub.3                                                                            N  CH      CCF.sub.3                                                                              0 65-67                                      20  Me H  OCF.sub.3                                                                           N  CCF.sub.3                                                                              CH      0 55-58                                      21  Me H  OCF.sub.3                                                                           N  CH      CCF.sub.3                                                                              0 102-105                                    22  Et H  OCF.sub.3                                                                           N  CH      CCF.sub.3                                                                              0 48- 50                                     23  Et H  OCF.sub.3                                                                           N  CCF.sub.3                                                                              CH      0 oil                                        24  Me H  OCF.sub.3                                                                           N  CH      COCHF.sub.2                                                                            0 101-103                                    25  Me H  OCF.sub.3                                                                           N  COCHF.sub.2                                                                            CH      0 61-64                                      26  MeO                                                                               H  CF.sub.3                                                                            N  CH      COCHF.sub.2                                                                            0 127-131                                    27  MeO                                                                               H  OCF.sub.3                                                                           N  CH      COCHF.sub.2                                                                            0 103-106                                    28  MeO                                                                               H  OCF.sub.3                                                                           N  COCHF.sub.2                                                                            CH      0 62-65                                      29  MeO                                                                               H  CF.sub.3                                                                            N  COCHF.sub.2                                                                            CH      0 80-84                                      30  Me Me OCHF.sub.2                                                                          N  CH      COCHF.sub.2                                                                            0 109-113                                    31  Me Me OCHF.sub.2                                                                          N  COCHF.sub.2                                                                            CH      0 85-88                                      32  MeO                                                                               H  OCF.sub.3                                                                           N  CH      CCF.sub.3                                                                              0 85-88                                      33  MeO                                                                               H  CF.sub.3                                                                            N  CH      CCF.sub.3                                                                              0 110-112                                    34  Et H  CF.sub.3                                                                            N  CCF.sub.3                                                                              CH      0 139-140                                    __________________________________________________________________________

TEST A

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), cheatgrass(Bromus secalinus), chickweed (Stellaria media), cocklebur (Xanthium pensylyanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica rapenapus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta yulgaris), velvetleaf (Abutilon theophrasti), wheat(Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxicsolvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in heightfrom two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 0 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

    TABLE A       Rate (2000 g/ha)  Rate (200 g/ha) Rate (50 g/ha) COMPOUND 1 3 4 5 6 1 3 4       5 6  30 30 30 30        POSTEMERGENCE PREEMERGENCE  POSTEMERGENCE PREEMERGENCE POSTEMERGENCE      PREEMERGENCE Barley 0 0 2 3 3 0 0 2 3 5 Barley 0 0 0 0 Barnyardgrass 1 1      3 -- -- 0 0 9 8 10  Barnyardgrass 0 0 0 0 Bedstraw 5 1 6 5 5 0 0 3 10  8      Bedstraw 0 0 0 0 Blackgrass 0 0 4 3 5 0 0 3 9 10  Blackgrass 0 0 0 0      Cheatgrass 0 0 2 2 6 0 0 4 9 10  Cheatgrass 0 0 0 0 Chickweed 4 1 7 5 7      0 2 10  10  10  Chickweed 0 0 0 0 Cocklebur 5 2 8 --  -- 0 -- -- -- --      Cocklebur 0 0 0 0 Corn 0 2 1 2 3 1 0 1 2 2 Corn 0 0 0 0 Cotton 8 3 5 3 6      0 0 0 4 6 Cotton 0 0 0 0 Crabgrass -- 1 2 2 3 1 2 10  10  10  Crabgrass      0 0 0 0 Giant foxtail 0 2 1 3 5 1 5 10  10  10  Giant foxtail 0 0 0 0      Lambsquarters 4 6 6 8 10  0 10  10  10  10  Lambsquarters 0 2 0 0      Morningglory 2 4 7 8 8 0 0 3 8 10  Morningglory 0 0 0 0 Nutsedge 1 5 1 0      -- 6 0 -- 2 3 Nutsedge 0 0 0 0 Rape 0 4 4 8 9 0 0 2 6 8 Rape 0 0 0 0      Rice 1 0 1 1 2 2 1 2 2 2 Rice 0 0 0 0 Sorghum 3 0 2 1 3 0 0 2 2 4      Sorghum 0 0 0 0 Soybean 5 5 6 6 7 0 0 2 1 5 Soybean 0 0 0 0 Sugar beet 6      9 8 8 9 0 0 9 10  10  Sugar beet 0 0 0 0 Velvetleaf 1 0 3 2 8 1 1 6 10      10  Velvetleaf 0 0 0 0 Wheat 0 0 0 1 2 0 0 3 3 6 Wheat 0 0 0 0 Wild      buckwheat 2 1 2 3 3 0 2 4 8 10  Wild oat 0 0 0 0 Wild oat 1 0 2 6 7 0 2      8 9 10      Rate (400 g/ha) COMPOUND 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 2      0 21 22 23 24 25 26 27 28 29 31 32 33 34        POSTEMERGENCE Barley 0 0 0 2 0 2 3 2 3 2 3 4  5 4 2 2 2 0 2 2 2 2 4 6      3 4 3 3 3 2 1 1 0 Barnyardgrass 0 2 1 1 -- -- 4 2 5 5 2 3 5 5 9 4 8 1 1      1 3 3 1 9 6 5 4 6 2 0 2 4 0 Bedstraw 0 3 1 2 2 3 7 4 6 7 6 7 6 6 7 3 5 4      5 2 5 6 7 9 8 9 8 8 7 0 4 7 0 Blackgrass 0 0 0 2 2 3 2 3 3 6 5 5 7 4 8 2      3 0 1 4 8 5 5 8 7 6 7 5 5 0 5 5 2 Cheatgrass 0 1 0 1 0 3 2 0 2 5 4 5 6 2      4 1 2 0 2 1 2 2 1 7 4 5 6 1 5 0 1 2 0 Chickweed 2 3 0 5 2 6 4 4 5 7 6 7      7 7 7 4 7 3 5 4 5 7 7 8 8 8 8 7 7 0 5 7 0 Cocklebur 2 4 2 4 -- -- -- --      -- -- -- -- -- 7 8 3 -- 2 4 3 7 7 5 7 8 7 6 7 6 0 6 6 0 Corn 0 1 0 1 2 1      1 2 2 3 2 2 2 3 5 2 2 2 0 1 2 1 1 5 2 2 2 2 2 0 1 2 0 Cotton 0 8 0 1 --      9 2 2 3 8 4 5 6 3 9 5 8 4 2 2 2 2 0 10 10 9 9 10 9 0 2 6 0 Crabgrass --      1 1 2 1 3 2 3 6 5 4 4 3 4 9 2 7 1 9 4 7 2 7 8 9 9 8 9 7 2 6 6 4 Giant      foxtail 0 2 1 2 2 3 3 2 2 6 3 5 5 4 5 3 5 2 1 2 3 2 3 2 2 3 6 6 3 1 2 3      0 Lambsquarters 3 5 2 4 4 8 9 3 9 6 7 8 7 10 10 10 10 1 8 -- 9 9 7 10 9      8 7 6 7 0 9 -- 0 Morningglory 2 6 4 5 3 4 8 7 8 7 2 4 4 8 8 3 6 3 8 5 9      7 5 7 8 8 8 9 7 3 6 7 0 Nutsedge 1 0 0 0 -- 1 1 -- 0 1 -- -- 2 2 7 -- 0      0 0 0 -- 0 0 1 2 -- 1 0 7 0 0 0 -- Rape 0 6 3 2 5 7 5 0 4 9 8 9 8 5 7 6      8 1 1 0 1 5 4 8 7 7 5 7 7 0 4 5 0 Rice 1 0 0 1 1 1 1 0 1 2 1 2 1 2 3 1 2      1 1 3 5 1 0 2 1 2 2 2 1 2 2 3 0 Sorghum 0 0 0 1 1 2 1 1 1 2 1 2 2 2 3 2      1 3 1 2 2 1 0 3 2 2 1 3 1 0 2 2 0 Soybean 1 5 4 6 6 7 7 5 8 5 5 7 6 7 8      7 5 5 3 3 6 5 3 8 8 4 5 4 3 0 4 5 0 Sugar beet 2 8 8 5 8 8 7 8 9 9 9 9 9      9 9 9 9 2 7 9 9 8 7 9 9 9 8 8 9 0 8 10 0 Velvetleaf 1 3 0 1 3 5 6 2 2 7      3 4 5 7 8 1 1 2 5 0 6 3 1 1 4 0 6 1 2 0 2 3 0 Wheat 0 0 0 0 0 2 3 2 2 2      4 3 4 3 3 0 3 0 1 1 3 2 1 6 4 3 2 2 2 0 0 1 0 Wild buckwheat 2 3 2 1 1 2      2 3 3 6 8 7 6 7 7 4 6 -- 10 4 7 4 -- -- -- -- -- -- -- -- 5 7 0 Wild oat      0 0 0 1 3 3 4 4 4 8 6 8 8 6 8 3 4 0 2 1 5 1 1 8 7 3 4 4 3 0 1 6 0        Rate (400 g/ha) COMPOUND 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18      19 20 21 22 23 24 25 26 27 28 29 31 32 33 34        PREEMERGENCE Barley 0 0 0 0 2 2 3 2 2 3 3 2 5 5 9 2 1 0 1 3 3 0 0 8 5      1 2 1 1 0 0 0 0 Barnyardgrass 0 0 0 1 7 7 8 5 10 8 7 2 7 10 10 8 9 0 2 6      9 9 6 10 10 3 5 9 3 0 4 5 0 Bedstraw 0 5 0 0 7 7 6 2 8 10 7 8 9 10 10 2      3 0 5 2 9 6 0 9 9 7 7 7 4 0 7 6 2 Blackgrass 0 0 0 0 10 9 9 10 10 5 8 9      10 9 10 10 9 0 9 8 10 7 7 10 9 9 10 10 9 0 10 2 0 Cheatgrass 0 0 0 2 9      10 4 8 10 5 8 7 10 9 10 4 6 0 5 2 5 4 3 10 10 10 10 3 2 0 4 2 0 Chickweed       0 7 0 10 10 9 3 3 7 9 9 10 10 10 10 10 9 0 5 9 10 1 0 9 9 10 9 9 7 0 9      9 0 Cocklebur -- 0 -- -- -- -- -- -- -- 2 4 1 2 5 5 2 0 0 0 1 1 0 0 0 0      0 0 0 0 0 0 0 0 Corn 0 0 0 1 3 1 1 2 2 2 2 1 5 3 3 1 2 0 1 0 5 1 0 3 3 2      1 1 1 0 1 2 0 Cotton 0 0 0 0 0 3 0 0 0 1 1 1 2 0 1 0 0 0 0 0 2 0 0 1 --      0 2 -- 0 0 2 3 0 Crabgrass 0 5 2 8 10 10 10 9 10 9 9 10 10 10 10 9 10 0      10 9 9 9 9 10 10 10 10 10 10 0 10 9 0 Giant foxtail 0 6 2 7 10 10 10 10      10 10 9 10 10 10 10 10 10 3 10 10 10 10 10 10 10 10 10 10 10 0 10 10 0      Lambsquarters 0 7 8 10 10 10 9 10 10 -- 10 -- 10 10 10 10 10 0 -- 4 10      -- -- 10 10 10 10 10 10 0 9 9 0 Morningglory 0 0 0 0 5 9 1 1 5 5 5 2 5 5      6 1 2 0 5 1 8 1 0 6 7 8 1 6 1 0 3 4 0 Nutsedge 0 0 0 --  0 3 0 0 3 -- 0      0 0 -- -- -- 5 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 Rape 0 1 0 0 7 6 3 2 2 10      7 4 10 6 10 2 2 0 2 1 2 1 0 10 9 2 2 3 2 0 5 5 0 Rice 1 0 0 1 1 0 1 0 2      1 1 1 1 1 1 2 0 0 0 2 1 1 0 1 2 2 1 0 1 0 0 1 0 Sorghum 0 0 0 1 1 2 1 10      3 2 1 1 5 2 2 2 1 0 1 1 3 2 0 6 2 2 1 1 0 0 1 2 0 Soybean 0 0 0 0 0 1 0      0 1 2 1 2 2 1 2 1 0 0 0 0 3 0 0 1 3 0 1 0 0 0 0 1 0 Sugar beet 0 2 0 2 9      9 7 8 8 10 9 7 10 10 10 9 9 0 8 7 9 5 5 10 10 10 9 9 8 0 8 7 0 Velvetleaf       0 0 0 0 6 5 1 2 10 2 5 1 3 7 10 1 0 0 1 1 1 0 0 7 7 3 0 0 0 0 3 0 0      Wheat 0 0 0 0 3 3 2 3 3 2 5 2 4 3 6 0 1 0 1 4 5 1 0 7 7 1 2 4 1 0 5 1 0      Wild buckwheat 0 0 0 5 6 4 4 4 8 7 9 8 7 7 10 9 4 -- 4 7 7 0 0 -- -- --      -- -- -- -- 0 3 2 Wild oat 0 2 0 4 9 9 9 9 9 7 8 9 9 10 10 6 9 0 6 7 10      7 4 10 9 8 7 8 7 0 5 7 0        Rate (100 g/ha) COMPOUND 2 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 2      2 23 24 25 26 27 28 29 31 32 33 34        POSTEMERGENCE Barley 0 1 0 0 0 2 1 2 2 2 2 0 0 0 0 0 1 1 2 3 1 3 2 2 3 1       0 1 0 Barnyardgrass 1 2 2 1 2 2 2 3 1 2 4 2 3 1 0 1 1 0 1 3 2 1 2 1 1 0      1 1 0 Bedstraw 2 7 4 3 3 6 4 5 4 3 3 2 3 1 3 1 3 5 3 7 6 7 5 6 6 0 3 6 0      Blackgrass 0 2 2 2 2 3 2 2 4 4 2 2 2 0 0 1 5 4 1 3 5 3 3 2 5 0 2 3 0      Cheatgrass 1 2 0 0 0 3 1 2 3 2 2 1 0 0 0 0 1 1 0 2 1 3 2 3 3 0 0 0 0      Chickweed 3 7 5 2 4 5 3 5 3 5 5 4 7 1 2 2 3 5 3 7 5 7 6 6 6 0 2 7 0      Cocklebur 2 -- -- -- -- -- -- -- -- 5 2 2 -- 0 3 1 5 3 2 3 6 7 3 2 6 0 3      2 0 Corn 1 1 1 1 1 2 1 2 2 1 3 1 2 1 0 1 1 0 0 2 1 2 1 1 1 0 1 1 0      Cotton 7 7 2 0 3 8 5 6 3 9 9 5 5 2 1 0 1 0 0 10 8 9 9 9 9 0 1 1 0      Crabgrass 1 2 1 2 4 4 2 3 2 3 7 2 3 1 5 3 6 1 2 8 6 4 6 4 5 2 4 1 0      Giant foxtail 1 2 1 1 1 3 1 4 2 2 3 2 3 1 1 2 1 1 2 2 2 2 2 2 2 0 1 1 0      Lambsquarters 3 5 4 2 4 5 3 5 5 9 10 6 10 1 -- 2 -- 3 1 -- 9 7 5 6 7 0 3      7 0 Morningglory 3 3 6 2 5 5 3 2 2 6 2 3 5 2 6 3 6 2 5 8 5 8 5 7 6 1 2 5      0 Nutsedge 0 0 0 0 0 0 1 1 0 0 0 0 1 0 0 0 0 0 0 -- 0 -- 1 0 0 0 -- 0 0      Rape 0 7 2 0 0 6 7 6 6 2 4 6 5 0 1 0 0 3 3 6 5 4 5 5 5 0 2 3 0 Rice 0 1      0 0 0 1 1 2 0 1 1 1 1 0 1 1 3 1 0 1 1 1 1 1 1 0 1 1 0 Sorghum 0 2 1 1 1      1 1 2 2 1 2 1 1 0 1 1 1 1 0 2 2 1 1 1 1 0 1 1 0 Soybean 4 5 4 3 7 4 4 4      6 3 7 5 6 2 2 3 6 4 2 6 7 3 3 3 3 0 3 3 0 Sugar beet 7 8 5 7 7 9 8 8 8 9      8 9 8 0 6 5 9 7 5 9 9 5 9 8 8 0 4 5 0 Velvetleaf 1 2 2 1 3 4 1 4 2 2 1 1      1 0 1 0 0 1 0 4 2 0 2 1 1 0 1 2 0 Wheat 0 2 0 0 0 3 1 1 2 2 2 0 0 0 0 0      1 0 0 3 1 2 2 1 1 0 0 0 0 Wild buckwheat 1 2 2 2 2 5 5 7 2 4 3 2 5 -- 4      2 3 1 0 -- -- -- -- -- -- -- 5 1 0 Wild oat 0 1 0 0 2 6 4 5 5 3 3 2 1 0      1 1 2 1 0 5 2 2 3 2 2 0 1 1 0        Rate (100 g/ha) COMPOUND 2 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 2      2 23 24 25 26 27 28 29 31 32 33 34        PREEMERGENCE Barley 0 2 0 0 2 2 2 1 1 2 4 0 0 0 0 0 0 0 0 5 2 0 0 0 0      0 0 0 0 Barnyardgrass 0 2 3 1 4 4 4 1 5 3 10 2 3 0 0 0 7 3 2 8 1 0 1 1 0      1 1 0 Bedstraw 2 6 2 0 3 4 2 3 3 3 10 1 2 -- 1 0 3 0 1 7 4 5 3 3 3 0 0 1      0 Blackgrass 0 6 8 7 9 5 5 5 4 6 10 0 3 0 5 1 9 3 3 8 5 2 3 8 3 0 2 2 0      Cheatgrass 0 7 2 3 9 6 4 3 5 6 10 0 2 0 0 0 2 2 2 8 3 2 1 1 0 0 0 0 0      Chickweed 0 8 0 0 2 6 3 5 8 2 10 0 7 0 0 8 5 0 0 8 9 3 3 5 1 0 0 7 0      Cocklebur 0 -- -- -- -- 0 -- 0 0 1 3 0 0 0 0 0 -- 0 0 0 0 0 0 0 0 0 0 --      0 Corn 0 1 1 0 1 1 1 1 1 1 1 1 1 0 0 0 2 0 0 2 1 0 0 0 0 0 0 1 0 Cotton      0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 2 0 0 0 1 0 0 0 0 0 -- 0 0 Crabgrass 1 7      9 8 9 9 7 9 9 9 10 9 10 -- 7 5 9 8 3 10 10 6 2 6 2 0 6 2 0 Giant foxtail      1 9 10 9 10 9 9 9 9 10 10 9 9 0 5 6 9 9 6 10 10 8 10 9 6 0 8 6 0      Lambsquarters 0 -- 0 3 5 10 8 0 10 10 10 0 10 0 0 0 2 5 2 9 10 10 10 2 2      0 0 0 0 Morningglory 0 1 0 0 2 1 0 0 1 1 6 1 0 0 0 3 1 0 0 1 1 0 2 1 0 0      1 2 0 Nutsedge 0 0 0 -- -- 0 0 0 0 0 -- 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0      0 0 Rape 0 2 2 0 0 1 1 1 7 1 6 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 0 0 0 Rice      0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 1 0 1 1 0 0 0 0 0 -- 0 0 Sorghum 0 1 1      0 0 1 1 0 1 0 1 0 1 0 0 0 0 0 0 2 1 0 0 0 0 0 0 0 0 Soybean 0 1 0 0 0 1      1 0 1 0 1 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 Sugar beet 0 4 4 4 7 8 7 5      6 9 9 8 7 0 1 1 6 3 3 9 9 8 7 7 3 0 0 0 0 Velvetleaf 0 0 0 0 1 0 1 0 1 1      3 0 0 0 0 0 0 0 0 3 2 0 0 0 0 0 0 0 0 Wheat 0 1 0 0 2 1 0 1 1 1 2 0 0 0      0 0 0 0 0 4 1 0 0 0 0 0 0 0 0 Wild buckwheat 0 7 0 2 2 5 7 0 2 5 9 2 0      -- 0 0 4 1 0 -- -- -- -- -- -- -- 0 2 0 Wild oat 0 4 3 4 9 5 4 4 8 8 8 2      3 0 0 3 9 1 2 9 7 5 5 6 3 0 3 5 0

TESTS B

The compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (paddy application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the paddy test. Water depth was approximately 2.5 cm for the paddy test and was maintained at this level for the duration of the test.

Plant species in the preemergence and postemergence tests consisted of barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), ducks salad (Heteranthera limosa), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthusretroflexus), rape (Brassica napus), ryegrass (Lolium multiflorum), sorghum (Sorghum bicolor), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus) and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus). All plant species were planted one day beforeapplication of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the paddytest consisted of barnyardgrass (Echinochloa crus-galli), rice (Oryza sativa), and umbrella sedge (Cyperus difformis).

All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty-one days after application of the test compound. Plant response ratings, summarized in Table B, were recorded on a 0 to 10 scale where 0 is no injury and 10 is complete control. A dash (-) response means no test result.

                  TABLE B                                                          ______________________________________                                                  Rate (500 g/ha)                                                                COMPOUND                                                                       5    9     15    21  24  5    9   15  21  24                          ______________________________________                                                  POSTEMERGENCE                                                                               PREEMERGENCE                                             Barley Igri                                                                               4      3     4   1   2   --   2   5   4   3                         Bedstraw   4      10    9   9   9   10   10  10  5   10                        Blackgrass 3      8     9   6   9   6    10  10  10  10                        Chickweed  5      10    9   9   9   10   10  10  9   10                        Corn       3      4     4   5   4   7    4   2   3   0                         Cotton     5      6     4   3   5   4    3   5   2   0                         Crabgrass  3      7     9   6   8   10   10  10  10  10                        Downy brome                                                                               1      4     5   --  2   --   6   10  4   10                        Duck salad 4      5     2   0   2   --   --  --  --  --                        Giant foxtail                                                                             4      6     6   3   5   10   10  10  10  10                        Lambsquarters                                                                             6      10    10  10  10  10   10  10  10  10                        Morningglory                                                                              6      7     10  8   8   8    4   8   3   6                         Pigweed    8      8     8   8   8   10   10  10  10  10                        Rape       5      7     9   6   6   10   10  10  4   4                         Ryegrass   0      3     4   2   1   6    10  10  5   10                        Sorghum    2      3     4   4   4   4    8   8   5   --                        Soybean    5      7     9   6   9   3    0   6   4   --                        Speedwell  10     10    10  10  10  10   10  10  10  10                        Sugar beet 8      10    9   10  10  10   9   10  10  10                        Velvetleaf 0      7     8   4   6   9    7   10  4   8                         Wheat      2      3     3   1   3   0    1   6   4   4                         Wild buckwheat                                                                            3      9     7   10  10  9    9   10  6   10                        Wild oat   4      7     6   3   10  3    10  10  10  10                        Barnyardgrass                                                                             5      10    9   9   10                                             Rice Japonica                                                                             2      6     6   5   4                                              Umbrella sedge                                                                            7      9     9   3   6                                              ______________________________________                                                  Rate (250 g/ha)                                                                COMPOUND                                                                       5    9     15    21  24  5    9   15  21  24                          ______________________________________                                                  POSTEMERGENCE                                                                               PREEMERGENCE                                             Barley Igri                                                                               2      3     2   1   2   2    1   3   2   2                         Bedstraw   3      8     9   9   9   7    10  10  5   0                         Blackgrass 2      7     9   6   9   6    10  10  10  10                        Chickweed  5      7     9   9   6   10   10  10  9   10                        Corn       3      3     3   4   3   7    3   0   2   0                         Cotton     4      6     3   3   4   3    0   4   0   0                         Crabgrass  3      6     9   6   8   10   10  10  10  10                        Downy brome                                                                               0      2     4   --  1   0    6   10  4   4                         Duck salad 2      3     1   0   1   --   --  --  --  --                        Giant foxtail                                                                             3      4     5   3   3   9    10  10  10  10                        Lambsquarters                                                                             4      10    10  10  9   10   10  10  8   10                        Morningglory                                                                              5      6     9   7   7   6    3   7   2   5                         Pigweed    6      8     8   8   8   10   10  10  10  10                        Rape       4      6     9   5   3   8    10  8   2   4                         Ryegrass   0      0     3   --  0   6    10  10  4   10                        Sorghum    2      2     3   4   3   3    7   7   5   --                        Soybean    4      7     8   5   3   3    0   3   2   0                         Speedwell  10     10    10  10  10  10   10  10  10  10                        Sugar beet 8      10    9   10  8   10   9   10  9   10                        Velvetleaf 0      6     7   4   5   8    7   8   4   6                         Wheat      1      2     2   --  2   --   --  3   1   4                         Wild buckwheat                                                                            2      7     6   10  10  8    8   10  6   10                        Wild oat   3      5     5   2   --  3    5   9   7   9                         Barnyardgrass                                                                             5      10    9   9   10                                             Rice Japonica                                                                             0      5     6   4   4                                              Umbrella sedge                                                                            6      8     8   1   5                                              ______________________________________                                                  Rate (125 g/ha)                                                                COMPOUND                                                                       5    9     15    21  24  5    9   15  21  24                          ______________________________________                                                  POSTEMERGENCE                                                                               PREEMERGENCE                                             Barley Igri                                                                               2      2     2   --  1   0    --  1   0   0                         Bedstraw   0      8     7   9   8   4    8   10  3   0                         Blackgrass 0      7     9   5   6   3    10  10  10  10                        Chickweed  3      7     9   7   --  8    8   10  5   10                        Corn       3      3     3   4   2   4    3   0   2   0                         Cotton     3      5     3   2   4   3    0   3   0   0                         Crabgrass  3      5     9   4   7   9    10  10  10  10                        Downy brome                                                                               0      0     3   0   0   0    4   6   4   4                         Duck salad 2      3     0   0   0   --   --  --  --  --                        Giant foxtail                                                                             3      3     4   2   0   9    10  10  9   10                        Lambsquarters                                                                             3      10    10  10  9   10   10  10  5   10                        Morningglory                                                                              5      6     9   7   5   4    2   6   2   0                         Pigweed    6      8     8   7   5   10   10  10  10  10                        Rape       4      5     8   3   2   5    7   4   0   0                         Ryegrass   0      0     2   0   0   2    5   10  3   9                         Sorghum    2      2     2   3   3   2    6   5   3   0                         Soybean    4      6     8   5   3   3    0   2   2   0                         Speedwell  10     10    10  10  10  10   10  10  10  10                        Sugar beet 6      8     9   9   6   10   9   10  5   9                         Velvetleaf 0      4     6   2   0   6    5   4   4   0                         Wheat      1      1     2   0   1   0    0   3   0   0                         Wild buckwheat                                                                            1      5     5   9   7   4    7   10  6   --                        Wild oat   3      3     4   0   3   3    3   8   5   9                         Barnyardgrass                                                                             4      10    9   9   10                                             Rice Japonica                                                                             0      3     4   2   3                                              Umbrella sedge                                                                            5      8     5   0   1                                              ______________________________________                                                  Rate (62 g/ha)                                                                 COMPOUND                                                                       5    9     15    21  24  5    9   15  21  24                          ______________________________________                                                  POSTEMERGENCE                                                                               PREEMERGENCE                                             Barley Igri                                                                               1      2     1   0   1   0    0   1   0   0                         Bedstraw   0      7     7   4   5   3    7   10  2   0                         Blackgrass 0      2     7   1   3   3    8   10  8   10                        Chickweed  2      6     8   4   5   5    6   10  5   5                         Corn       3      2     2   3   2   3    3   0   0   0                         Cotton     3      4     3   2   3   2    0   0   0   0                         Crabgrass  3      4     9   2   7   8    10  10  9   10                        Downy brome                                                                               0      0     2   0   0   0    2   4   3   0                         Duck salad 1      2     0   0   0   --   --  --  --  --                        Giant foxtail                                                                             3      3     3   2   0   8    10  10  8   10                        Lambsquarters                                                                             3      10    10  9   9   10   6   10  5   9                         Morningglory                                                                              3      6     7   5   5   3    1   5   0   0                         Pigweed    6      7     7   5   5   9    10  10  9   10                        Rape       3      5     7   2   --  4    3   4   0   0                         Ryegrass   0      0     2   0   0   0    5   9   2   3                         Sorghum    2      1     2   3   2   0    4   4   2   0                         Soybean    4      6     7   5   2   0    0   0   0   0                         Speedwell  9      10    10  10  10  10   10  10  8   10                        Sugar beet 6      8     8   9   6   7    8   10  5   5                         Velvetleaf 0      3     6   2   0   4    0   3   4   0                         Wheat      1      0     2   0   0   0    0   3   0   0                         Wild buckwheat                                                                            0      5     4   7   6   4    5   10  2   9                         Wild oat   3      2     3   0   3   3    1   5   4   3                         Barnyardgrass                                                                             3      10    9   9   10                                             Rice Japonica                                                                             0      0     3   0   2                                              Umbrella sedge                                                                            0      5     2   0   0                                              ______________________________________                                                  Rate (31 g/ha)                                                                 COMPOUND                                                                       5    9     15    21  24  5    9   15  21  24                          ______________________________________                                                  POSTEMERGENCE                                                                               PREEMERGENCE                                             Barley Igri                                                                               1      1     1   0   --  0    0   1   0   0                         Bedstraw   0      0     5   4   5   0    0   5   0   0                         Blackgrass 0      0     4   --  2   0    5   9   8   10                        Chickweed  0      5     8   4   4   5    0   9   5   1                         Corn       2      1     2   3   2   0    0   0   0   0                         Cotton     2      3     3   2   3   0    0   0   0   0                         Crabgrass  3      3     8   2   7   7    9   10  5   10                        Downy brome                                                                               0      0     2   0   0   0    0   1   3   0                         Duck salad 0      0     0   0   0   --   --  --  --  --                        Giant foxtail                                                                             3      3     3   0   0   7    7   10  6   7                         Lambsquarters                                                                             2      7     10  9   6   7    3   10  5   2                         Morningglory                                                                              2      4     6   5   0   3    0   0   0   0                         Pigweed    5      7     7   5   5   9    10  10  3   8                         Rape       2      3     6   0   --  0    0   1   0   0                         Ryegrass   0      0     2   0   0   0    0   5   2   3                         Sorghum    2      1     2   2   2   0    3   4   0   0                         Soybean    3      4     6   4   0   0    0   0   0   0                         Speedwell  4      9     10  10  10  9    9   10  8   9                         Sugar beet 5      6     7   9   6   2    0   8   2   3                         Velvetleaf 0      0     4   0   0   0    0   2   2   0                         Wheat      0      0     1   0   0   0    0   3   0   0                         Wild buckwheat                                                                            0      0     2   4   3   4    2   7   0   0                         Wild oat   2      2     2   0   0   2    0   4   2   0                         Barnyardgrass                                                                             0      9     9   5   7                                              Rice Japonica                                                                             0      0     2   0   1                                              Umbrella sedge                                                                            0      3     0   0   0                                              ______________________________________                                    

TEST C

Seeds of barnyardgrass (Echinochloa crus-galli), cassia (Cassia obtusifolia), cocklebur (Xanthium pensylvanicum), common ragweed (Ambrosiaelatior), corn (Zea mays), cotton (Gossypium hirsutam), crabgrass (Digitaria spp.), fall panicum (Panicum dicholomiflorum), giant foxtail (Setaria faberii), green foxtail (Setaria vividis), jimson wee (Datura stramonium), johnson grass (Sorghum halepense), morningglory (Ipomoea spp.), prickly sida (Sida spinosa), signalgrass (Brachiaria platyphylla), soybean (Glycine max), velvetleaf (Abutilon theophrasti), wild proso (Pancium miliaceum) and purple nutsedge (Cyperus rotundus) tubers were planted into a silt loam soil. Test chemicals, dissolved in a non-phytotoxic solvent, were then applied to the soil surface within one day after the seeds were planted. Pots receiving these preemergence treatments were placed in the greenhouse and maintained according to routine greenhouse procedures.

Treated plants and untreated controls were maintained in the greenhouse approximately 21 days after application of the test compound. Visual evaluations of plant injury responses were then recorded. Plant response ratings, summarized in Table C, are reported on a 0 to 10 scale where 0 isno effect and 10 is complete control.

                  TABLE C                                                          ______________________________________                                                   Rate                                                                           (500 g/ha)           (250 g/ha)                                                COMPOUND                                                                       9                    9      15                                       ______________________________________                                                   PREEMERGENCE                                                         Barnyardgrass                                                                              8         Barnyardgrass                                                                               7    10                                     Cassia      6         Cassia       0    8                                      Cocklebur   0         Cocklebur    0    0                                      Common Ragweed                                                                             8         Common Rag-  8    10                                     Corn G4689A 3         weed                                                     Cotton      0         Corn G4689A  1    2                                      Crabgrass   10        Cotton       0    0                                      Fall Panicum                                                                               10        Crabgrass    10   10                                     Giant Foxtail                                                                              10        Fall Panicum 10   10                                     Green Foxtail                                                                              10        Giant Foxtail                                                                               10   10                                     Jimson weed 8         Green Foxtail                                                                               10   10                                     Johnson Grass                                                                              9         Jimson weed  6    7                                      Morningglory                                                                               7         Johnson Grass                                                                               6    6                                      Prickly sida                                                                               7         Nutsedge     6    --                                     Signalgrass 10        Prickly sida 5    6                                      Soybean     1         Signalgrass  10   10                                     Velvetleaf  4         Velvetleaf   4    6                                      Wild Proso  9         Wild Proso   9    9                                      ______________________________________                                                  Rate                  Rate                                                     (125 g/ha)            (62 g/ha)                                                COMPOUND                                                                       9    15                   9    15                                     ______________________________________                                                  PREEMERGENCE                                                          Barnyardgrass                                                                             5      8      Barnyardgrass                                                                               2   7                                    Cassia     0      0      Cassia      0    0                                    Cocklebur  0      0      Cocklebur   --   0                                    Common Rag-                                                                               1      0      Common Ragweed                                                                             0    0                                    weed                     Corn G4689A --   1                                    Corn G4689A                                                                               1      1      Cotton      0    --                                   Cotton     0      --     Crabgrass   10   10                                   Crabgrass  10     10     Fall Panicum                                                                               0    8                                    Fall Panicum                                                                              1      10     Giant Foxtail                                                                              9    10                                   Giant Foxtail                                                                             9      10     Green Foxtail                                                                              7    10                                   Green Foxtail                                                                             10     10     Jimson weed 0    0                                    Jimson weed                                                                               2      1      Johnson Grass                                                                              --   6                                    Johnson Grass                                                                             1      6      Morningglory                                                                               0    --                                   Nutsedge   0      --     Nutsedge    0    2                                    Prickly sida                                                                              0      6      Prickly sida                                                                               0    0                                    Signalgrass                                                                               --     10     Signalgrass --   10                                   Soybean    0      --     Soybean     0    --                                   Velvetleaf 0      2      Velvetleaf  0    0                                    Wild Proso 8      8      Wild Proso  7    8                                    ______________________________________                                                   Rate                 Rate                                                      (31 g/ha)            (16 g/ha)                                                 COMPOUND                                                                       9    15                  15                                          ______________________________________                                                   PREEMERGENCE                                                         Barnyardgrass                                                                              0      2      Barnyardgrass                                                                             0                                         Cassia      0      0      Cassia     0                                         Cocklebur   0      0      Cocklebur  0                                         Common Ragweed                                                                             0      0      Common Rag-                                                                               0                                         Corn G4689A --     1      weed                                                 Cotton      0      0      Cotton     0                                         Crabgrass   2      9      Crabgrass  6                                         Fall Panicum                                                                               --     0      Fall Panicum                                                                              0                                         Giant Foxtail                                                                              8      8      Giant Foxtail                                                                             2                                         Green Foxtail                                                                              6      8      Green Foxtail                                                                             4                                         Jimson weed 0      0      Jimson weed                                                                               0                                         Johnson Grass                                                                              0      6      Johnson Grass                                                                             2                                         Morningglory                                                                               --     0      Morningglory                                                                              0                                         Prickly sida                                                                               0      0      Nutsedge   0                                         Signalgrass --     9      Prickly sida                                                                              0                                         Soybean     0      0      Signalgrass                                                                               0                                         Velvetleaf  0      0      Soybean    0                                         Wild Proso  6      7      Velvetleaf 0                                                                   Wild Proso 6                                         ______________________________________                                    

TEST D

Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Japonica rice (Oryza sativa) seedlings at the 2.0 to2.5 leaf stage, seeds selected from barnyardgrass (Echinochloa crus-gali), umbrella sedge (Cyperus difformis), and tubers selected from arrowhead (Sagittaria spp.), waterchestnut (Eleocharis spp.), were planted into thissoil. After planting, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent and applied directly to the paddy water. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table D, are reported on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

                  TABLE D                                                          ______________________________________                                                 COMPOUND                                                                       9                                                                      ______________________________________                                                     Rate (500 g/ha)                                                                          Rate (64 g/ha)                                                       PADDY                                                              Arrowhead     0           0                                                    Barnyardgrass 10          3                                                    Japonica rice 4           1                                                    Umbrella sedge                                                                               6           4                                                    Waterchestnut 0           0                                                                  Rate (250 g/ha)                                                                            Rate (32 g/ha)                                                   PADDY                                                              Arrowhead     0           0                                                    Barnyardgrass 10          1                                                    Japonica rice 3           0                                                    Umbrella sedge                                                                               4           3                                                    Waterchestnut 0           0                                                                  Rate (125 g/ha)                                                                PADDY                                                            Arrowhead     0                                                                Barnyardgrass 9                                                                Japonica rice 2                                                                Umbrella sedge                                                                               3                                                                Waterchestnut 0                                                                ______________________________________                                    

TEST E

Plastic pots were partially filled with silt loam soil. The soil was then flooded with water, Japonica rice (Oryza sativa) sprouted seeds and 1.5 leaf transplants were planted in the soil. Seeds of barnyardgrass (Echinochloa crus-galli) were planted in saturated soil and plants grown to the 1 leaf, 2 leaf and 3 leaf stages for testing. At testing, the waterlevel for all plantings was raised to 2 cm above the soil surface. Chemicaltreatments were formulated in a non-phytotoxic solvent and applied directlyto the paddy water. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarize in Table E are reported on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

                  TABLE E                                                          ______________________________________                                                     COMPOUND                                                                       9                                                                  ______________________________________                                                     Rate (500 g/ha)                                                                          Rate (125 g/ha)                                                      Flood                                                              1-LF B.Y. Grass                                                                              10          9                                                    2-LF B.Y. Grass                                                                              9           5                                                    3-lf B.Y. Grass                                                                              8           3                                                    Jap Direct Seed                                                                              3           1                                                    Jap Rice Eff  3           0                                                                  Rate (250 g/ha)                                                                            Rate (64 g/ha)                                                   Flood                                                              1-LF B.Y. Grass                                                                              10          8                                                    2-LF B.Y. Grass                                                                              8           4                                                    3-If B.Y. Grass                                                                              9           2                                                    Jap Direct Seed                                                                              1           1                                                    Jap Price Eff 1           0                                                                  Rate (32 g/ha)                                                                             Rate (8 g/ha)                                                    Flood                                                              1-LF B.Y. Grass                                                                              6           0                                                    2-LF B.Y. Grass                                                                              2           0                                                    3-lf B.Y. Grass                                                                              0           0                                                    Jap Direct Seed                                                                              0           0                                                    Jap Rice Eff  0           0                                                                  Rate (16 g/ha)                                                                 Flood                                                            1-LF B.Y. Grass                                                                              0                                                                2-LF B.Y. Grass                                                                              0                                                                3-If B.Y. Grass                                                                              0                                                                Jap Direct Seed                                                                              0                                                                Jap Rice Eff  0                                                                ______________________________________                                    

TEST F

Compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were in the one-to-four leafstage (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test: Test compounds were applied within approximately one day after planting seeds for the preemergence test. Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test.All plant species were grown using normal greenhouse practices. Crop and weed species include winter barley (Hordeum vulgare cv. `Igri`), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), downy brome (Bromus tectorum), field violet (Viola arvensis), green foxtail (Setaria viridis), kochia (Kochia scoparia), lambsquarters (Chenopodium album), Persian speedwell (Veronica persica), rape (Brassica napus cv. `Jet Neuf`), ryegrass (Lolium multiflorum), sugarbeet (Beta vulgaris cv. `US1` ), sunflower (Helianthus annuus cv. `Russian Giant`), spring wheat (Triticum aestivum cv. `ERA`), winter wheat (Triticum eastivum cv. `Talent`), wild buckwheat (Polygonum conyolyulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), and wild radish (Raphanus raphanistrum). Blackgrass and wild oat were treated postemergence at two growth stages. The first stage (1) was when the plants had two to three leaves. The second stage (2) was then the plants had approximately four leaves or in the initial stages of tillering. Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table F, are based upon a 0 to 10 scale where 0 is no effectand 10 is complete control. A dash response (-) means no test result.

                  TABLE F                                                          ______________________________________                                                  Rate (500 g/ha)                                                                COMPOUND                                                                         9   15               9    15                                        ______________________________________                                                  POSTEMERGENCE                                                                               PREEMERGENCE                                             Blackgrass (1)                                                                              --    7              10   10                                      Blackgrass (2)                                                                              --    5              10   10                                      Chickweed    0     3              10   10                                      Downy brome  --    2              10   10                                      Field violet 4     10             10   10                                      Galium (1)   0     2              10   10                                      Galium (2)   --    --             --   10                                      Green foxtail                                                                               --    6              10   10                                      Kochia       8     6              10   10                                      Lambsquarters                                                                               7     10             10   10                                      Persn Speedwell                                                                             6     10             10   10                                      Rape         --    10             9    10                                      Ryegrass     --    3              10   10                                      Sugar beet   8     9              10   10                                      Sunflower    7     10             0    10                                      Wheat (Spring)                                                                              0     3              4    4                                       Wheat (Winter)                                                                              --    2              3    4                                       Wild buckwheat                                                                              2     2              10   10                                      Wild mustard 7     10             9    10                                      Wild oat (1) --    4              10   10                                      Wild oat (2) --    4              10   10                                      Wild radish  7     9              10   10                                      Winter Barley                                                                               --    2              4    4                                       ______________________________________                                                  Rate (250 g/ha)                                                                COMPOUND                                                                         9   15               9    15                                        ______________________________________                                                  POSTEMERGENCE                                                                               PREEMERGENCE                                             Blackgrass (1)                                                                              0     3              8    10                                      Blackgrass (2)                                                                              0     3              8    10                                      Chickweed    0     0              10   10                                      Downy brome  0     0              9    10                                      Field violet 2     9              10   10                                      Galium (1)   0     0              10   10                                      Galium (2)   --    --             --   10                                      Green foxtail                                                                               4     4              10   10                                      Kochia       6     4              7    10                                      Lambsquarters                                                                               5     8              10   10                                      Persn Speedwell                                                                             4     10             10   10                                      Rape         --    10             8    10                                      Ryegrass     0     0              10   10                                      Sugar beet   6     6              10   10                                      Sunflower    6     10             0    10                                      Wheat (Spring)                                                                              0     0              2    2                                       Wheat (Winter)                                                                              0     0              2    2                                       Wild buckwheat                                                                              0     0              10   10                                      Wild mustard 4     8              7    10                                      Wild oat (1) 2     2              8    10                                      Wild oat (2) 3     2              10   9                                       Wild radish  3     8              8    10                                      Winter Barley                                                                               0     0              2    2                                       ______________________________________                                                  Rate (125 g/ha)                                                                COMPOUND                                                                         9   15               9    15                                        ______________________________________                                                  POSTEMERGENCE                                                                               PREEMERGENCE                                             Blackgrass (1)                                                                              0     0              6    10                                      Blackgrass (2)                                                                              0     0              6    10                                      Chickweed    0     0              8    10                                      Downy brome  0     0              6    7                                       Field violet 0     8              10   10                                      Galium (1)   0     0              8    8                                       Galium (2)   --    --             --   8                                       Green foxtail                                                                               2     2              10   10                                      Kochia       3     2              3    8                                       Lambsquarters                                                                               2     5              8    10                                      Persn Speedwell                                                                             2     7              10   10                                      Rape         --    9              6    7                                       Ryegrass     0     0              8    8                                       Sugar beet   4     3              8    10                                      Sunflower    3     10             0    9                                       Wheat (Spring)                                                                              0     0              0    0                                       Wheat (Winter)                                                                              0     0              0    0                                       Wild buckwheat                                                                              0     0              6    8                                       Wild mustard 0     5              3    10                                      Wild oat (1) 0     0              6    8                                       Wild oat (2) 0     0              7    8                                       Wild radish  0     4              6    7                                       Winter Barley                                                                               0     0              0    0                                       ______________________________________                                                  Rate (64 g/ha)                                                                 COMPOUND                                                                         9   15               9    15                                        ______________________________________                                                  POSTEMERGENCE                                                                               PREEMERGENCE                                             Blackgrass (1)                                                                              0                    4    8                                       Blackgrass (2)                                                                              0                    4    8                                       Chickweed    0                    5    7                                       Downy brome  0                    4    3                                       Field violet 0                    8    10                                      Galium (1)   0                    4    4                                       Galium (2)   --                   --   5                                       Green foxtail                                                                               0                    10   10                                      Kochia       0                    0    4                                       Lambsquarters                                                                               0                    6    10                                      Persn Speedwell                                                                             0                    6    10                                      Rape         --                   4    5                                       Ryegrass     0                    3    6                                       Sugar beet   3                    6    9                                       Sunflower    0                    0    4                                       Wheat (Spring)                                                                              0                    0    0                                       Wheat (Winter)                                                                              0                    0    0                                       Wild buckwheat                                                                              0                    2    3                                       Wild mustard 0                    0    7                                       Wild oat (1) 0                    4    6                                       Wild oat (2) 0                    5    5                                       Wild radish  0                    2    3                                       Winter Barley                                                                               0                    0    0                                       ______________________________________                                                  Rate (32 g/ha)                                                                              Rate (16 g/ha)                                                    COMPOUND                                                                         9   15               9    15                                        ______________________________________                                                  POSTEMERGENCE                                                                               PREEMERGENCE                                             Blackgrass (1)                                                                              0     4              0    2                                       Blackgrass (2)                                                                              2     5              0    2                                       Chickweed    2     2              0    0                                       Downy brome  0     0              0    0                                       Field violet 4     9              0    6                                       Galium (1)   0     3              0    0                                       Galium (2)   --    2              --   0                                       Green foxtail                                                                               7     9              3    4                                       Kochia       0     0              0    0                                       Lambsquarters                                                                               2     8              0    5                                       Persn Speedwell                                                                             3     10             0    7                                       Rape         2     4              0    2                                       Ryegrass     0     3              0    0                                       Sugar beet   3     7              0    3                                       Sunflower    0     2              0    0                                       Wheat (Spring)                                                                              0     0              0    0                                       Wheat (Winter)                                                                              0     0              0    0                                       Wild buckwheat                                                                              0     0              0    0                                       Wild mustard 0     4              0    2                                       Wild oat (1) 2     3              0    0                                       Wild oat (2) 2     2              0    0                                       Wild radish  0     2              0    0                                       Winter Barley                                                                               0     0              0    0                                       ______________________________________                                     

What is claimed is:
 1. A compound of the formula ##STR29## wherein X is CH;Y is N; Z is N or CR⁵ ; Q is N or CR⁵ ; R is C₁ -C₄ alkyl, C₂ -C₄ alkoxyalkyl, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, C₁ -C₃ alkylamino or N(C₁ -C₃ alkyl) (C₁ -C₃ alkyl); R¹ is H, F, Cl or CH₃ ; R² is H, halogen, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; R³ is H, halogen, C₁ -C₄ alkyl, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl, C₁ -C₄ haloalkyl, C₃ -C₄ halocycloalkyl, C₂ -C₄ haloalkenyl, C₂ -C₄ haloalkynyl, OR⁶, S(O)_(n) R⁷ or CN; R⁵ is C₁ -C₄ haloalkyl, C₃ -C₅ halocycloalkyl, C₂ -C₄ haloalkenyl, C₂ -C₄ haloalkynyl, OR⁶, S(O)_(n) R⁷ or halogen; R⁶ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, C₁ -C₄ haloalkyl, C₂ -C₄ haloalkenyl or C₂ -C₄ haloalkynyl; R⁷ is C₁ -C₂ alkyl or C₁ -C₂ haloalkyl; and n is 0, 1 or 2;or their mono N-oxides or their agriculturally suitable salts, provided that: (a) when Z is N, then Q is CR⁵ ; and (b) when Q is N, then Z is CR⁵.
 2. The compounds of claim 1 wherein R¹ is H or F; and R² is H or F.
 3. The compounds of claim 2 whereinR³ is F, Cl, Br, C₁ -C₄ haloalkyl, OR⁶, S(O)_(n) R⁷ or CN; and n is O; or their mono N-oxides.
 4. The compounds of claim 3 whereinR is C₁ -C₃ alkyl, C₂ -C₃ alkoxyalkyl, C₂ -C₃ alkenyl, C₂ -C₃ alkynyl, C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₁ -C₂ alkylamino a N(C₁ -C₂ alkyl) (C₁ -C₂ alkyl); R⁶ is C₁ -C₃ alkyl, allyl, propargyl, C₁ -C₃ haloalkyl, C₂ -C₃ haloalkenyl.
 5. The compounds of claim 4 wherein Z is N.
 6. The compound of claim 1 which is: 7-methyl-3-(2,2,2-trifluoroethoxy)-5-[3-(trifluoromethyl)phenyl]-1,2,4-benzotriazine 1-oxide.
 7. The compound of claim 1 which is: 7-methyl-3-(2,2,2-trifluoroethoxy)-5-[3-(trifluoromethyl)phenyl]-1,2,4-benzotriazine.
 8. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
 9. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
 10. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
 11. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
 12. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
 13. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim, 6 and at least one of the following: surfactant, solid or liquid diluent.
 14. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.
 15. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 1. 16. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 2. 17. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 3. 18. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 4. 19. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 5. 20. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 6. 21. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 7. 